CA1092113A - Benzylamines - Google Patents
BenzylaminesInfo
- Publication number
- CA1092113A CA1092113A CA183,899A CA183899A CA1092113A CA 1092113 A CA1092113 A CA 1092113A CA 183899 A CA183899 A CA 183899A CA 1092113 A CA1092113 A CA 1092113A
- Authority
- CA
- Canada
- Prior art keywords
- hydroxy
- dibromo
- formula
- compound
- hal
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 150000003939 benzylamines Chemical class 0.000 title claims abstract description 8
- 150000001875 compounds Chemical class 0.000 claims abstract description 193
- 238000000034 method Methods 0.000 claims abstract description 124
- 230000008569 process Effects 0.000 claims abstract description 124
- 238000002360 preparation method Methods 0.000 claims abstract description 54
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 326
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 143
- -1 morpholino-carbonylmethyl Chemical group 0.000 claims description 84
- 238000006243 chemical reaction Methods 0.000 claims description 81
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 72
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 60
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 46
- 230000009467 reduction Effects 0.000 claims description 46
- 239000002904 solvent Substances 0.000 claims description 46
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 45
- 125000004432 carbon atom Chemical group C* 0.000 claims description 42
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 41
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 40
- 229910052794 bromium Inorganic materials 0.000 claims description 40
- 125000000217 alkyl group Chemical group 0.000 claims description 38
- AGVKXDPPPSLISR-UHFFFAOYSA-N n-ethylcyclohexanamine Chemical compound CCNC1CCCCC1 AGVKXDPPPSLISR-UHFFFAOYSA-N 0.000 claims description 37
- 239000002253 acid Substances 0.000 claims description 34
- 150000001412 amines Chemical class 0.000 claims description 33
- 239000012279 sodium borohydride Substances 0.000 claims description 31
- 229910000033 sodium borohydride Inorganic materials 0.000 claims description 31
- 239000011541 reaction mixture Substances 0.000 claims description 30
- 150000003254 radicals Chemical group 0.000 claims description 27
- SPUZPJKEJXIRSF-UHFFFAOYSA-N 2,4-dibromo-6-(bromomethyl)phenol Chemical compound OC1=C(Br)C=C(Br)C=C1CBr SPUZPJKEJXIRSF-UHFFFAOYSA-N 0.000 claims description 24
- VAYGTMNZLZAUDL-UHFFFAOYSA-N 2,6-dibromo-4-(bromomethyl)phenol Chemical compound OC1=C(Br)C=C(CBr)C=C1Br VAYGTMNZLZAUDL-UHFFFAOYSA-N 0.000 claims description 24
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 23
- 235000019253 formic acid Nutrition 0.000 claims description 23
- 239000000460 chlorine Substances 0.000 claims description 22
- 229910052801 chlorine Inorganic materials 0.000 claims description 22
- 125000002252 acyl group Chemical group 0.000 claims description 20
- 229930040373 Paraformaldehyde Natural products 0.000 claims description 19
- 230000003301 hydrolyzing effect Effects 0.000 claims description 18
- 239000000126 substance Substances 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 239000001257 hydrogen Substances 0.000 claims description 17
- AXRZRBIBAABFEA-UHFFFAOYSA-N 2,4-dibromo-6-(hydroxymethyl)phenol Chemical compound OCC1=CC(Br)=CC(Br)=C1O AXRZRBIBAABFEA-UHFFFAOYSA-N 0.000 claims description 16
- CSKKJEAMSBKJFT-UHFFFAOYSA-N 2,4-dibromo-6-[[cyclohexyl(ethyl)amino]methyl]phenol Chemical compound C1CCCCC1N(CC)CC1=CC(Br)=CC(Br)=C1O CSKKJEAMSBKJFT-UHFFFAOYSA-N 0.000 claims description 16
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 16
- 239000007795 chemical reaction product Substances 0.000 claims description 16
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 15
- IMLXLGZJLAOKJN-UHFFFAOYSA-N 4-aminocyclohexan-1-ol Chemical compound NC1CCC(O)CC1 IMLXLGZJLAOKJN-UHFFFAOYSA-N 0.000 claims description 14
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims description 14
- 238000009835 boiling Methods 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 14
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims description 13
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
- 230000007062 hydrolysis Effects 0.000 claims description 13
- 238000006460 hydrolysis reaction Methods 0.000 claims description 13
- 239000012280 lithium aluminium hydride Substances 0.000 claims description 13
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 12
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 12
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 12
- 229920002866 paraformaldehyde Polymers 0.000 claims description 12
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims description 10
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 10
- 150000001408 amides Chemical class 0.000 claims description 10
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 claims description 10
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 10
- NIQIPYGXPZUDDP-NTSWFWBYSA-N (1r,3s)-3-aminocyclohexan-1-ol Chemical compound N[C@H]1CCC[C@@H](O)C1 NIQIPYGXPZUDDP-NTSWFWBYSA-N 0.000 claims description 9
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 9
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 9
- 125000005843 halogen group Chemical group 0.000 claims description 9
- 230000026030 halogenation Effects 0.000 claims description 9
- 238000005658 halogenation reaction Methods 0.000 claims description 9
- 125000006239 protecting group Chemical group 0.000 claims description 9
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 8
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 7
- YZCKVEUIGOORGS-UHFFFAOYSA-N Hydrogen atom Chemical class [H] YZCKVEUIGOORGS-UHFFFAOYSA-N 0.000 claims description 7
- 125000004423 acyloxy group Chemical group 0.000 claims description 7
- 125000004429 atom Chemical group 0.000 claims description 7
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 7
- 229910052740 iodine Inorganic materials 0.000 claims description 7
- 239000000395 magnesium oxide Substances 0.000 claims description 7
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 claims description 7
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 claims description 7
- 150000007524 organic acids Chemical class 0.000 claims description 7
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 7
- FAXWFCTVSHEODL-UHFFFAOYSA-N 2,4-dibromophenol Chemical compound OC1=CC=C(Br)C=C1Br FAXWFCTVSHEODL-UHFFFAOYSA-N 0.000 claims description 6
- JHZOXYGFQMROFJ-UHFFFAOYSA-N 3,5-dibromo-2-hydroxybenzaldehyde Chemical compound OC1=C(Br)C=C(Br)C=C1C=O JHZOXYGFQMROFJ-UHFFFAOYSA-N 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 230000002152 alkylating effect Effects 0.000 claims description 6
- 150000002431 hydrogen Chemical class 0.000 claims description 6
- 229910052987 metal hydride Inorganic materials 0.000 claims description 6
- 150000004681 metal hydrides Chemical class 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- RVVVBIRTEHDWSZ-UHFFFAOYSA-N 6,8-dibromo-2-methyl-4H-1,3-benzodioxine Chemical compound BrC1=CC(Br)=C2OC(C)OCC2=C1 RVVVBIRTEHDWSZ-UHFFFAOYSA-N 0.000 claims description 5
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 5
- 235000019270 ammonium chloride Nutrition 0.000 claims description 5
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
- 239000003054 catalyst Substances 0.000 claims description 5
- 230000002140 halogenating effect Effects 0.000 claims description 5
- 150000007522 mineralic acids Chemical class 0.000 claims description 5
- 125000000542 sulfonic acid group Chemical group 0.000 claims description 5
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 claims description 5
- KLERNTFVTLXLIO-UWVGGRQHSA-N 2,6-dibromo-4-[[[(1S,3S)-3-hydroxycyclohexyl]amino]methyl]phenol Chemical compound C1[C@@H](O)CCC[C@@H]1NCC1=CC(Br)=C(O)C(Br)=C1 KLERNTFVTLXLIO-UWVGGRQHSA-N 0.000 claims description 4
- WGYPFUIIGCOOCK-UHFFFAOYSA-N 2-[[cyclohexyl(ethyl)amino]methyl]phenol Chemical compound C1CCCCC1N(CC)CC1=CC=CC=C1O WGYPFUIIGCOOCK-UHFFFAOYSA-N 0.000 claims description 4
- TWEVQGUWCLBRMJ-UHFFFAOYSA-N 3-hydroxycyclohexanone Chemical compound OC1CCCC(=O)C1 TWEVQGUWCLBRMJ-UHFFFAOYSA-N 0.000 claims description 4
- XLWJVYYSWQWBNB-UHFFFAOYSA-N 4-(aminomethyl)-2,6-dibromophenol Chemical compound NCC1=CC(Br)=C(O)C(Br)=C1 XLWJVYYSWQWBNB-UHFFFAOYSA-N 0.000 claims description 4
- YUDRVAHLXDBKSR-UHFFFAOYSA-N [CH]1CCCCC1 Chemical compound [CH]1CCCCC1 YUDRVAHLXDBKSR-UHFFFAOYSA-N 0.000 claims description 4
- 239000003377 acid catalyst Substances 0.000 claims description 4
- 125000003277 amino group Chemical group 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- GEDPQKGMHLHFOZ-XYPYZODXSA-N chembl2106163 Chemical compound C1C[C@@H](O)CC[C@@H]1NCC1=CC(Br)=CC(Br)=C1O GEDPQKGMHLHFOZ-XYPYZODXSA-N 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 150000004820 halides Chemical class 0.000 claims description 4
- ZHQSRFOPWMXBRO-UHFFFAOYSA-N iodosylbenzene dihydrochloride Chemical compound Cl.Cl.O=IC1=CC=CC=C1 ZHQSRFOPWMXBRO-UHFFFAOYSA-N 0.000 claims description 4
- 235000005985 organic acids Nutrition 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- HQAAWQKUJZFQLK-RQJHMYQMSA-N (1s,3r)-3-(methylamino)cyclohexan-1-ol Chemical compound CN[C@@H]1CCC[C@H](O)C1 HQAAWQKUJZFQLK-RQJHMYQMSA-N 0.000 claims description 3
- NIQIPYGXPZUDDP-WDSKDSINSA-N (1s,3s)-3-aminocyclohexan-1-ol Chemical compound N[C@H]1CCC[C@H](O)C1 NIQIPYGXPZUDDP-WDSKDSINSA-N 0.000 claims description 3
- UAIGGQBWXKBWOB-UHFFFAOYSA-N (3,5-dibromo-4-hydroxyphenyl)methyl acetate Chemical compound C(C)(=O)OCC1=CC(=C(C(=C1)Br)O)Br UAIGGQBWXKBWOB-UHFFFAOYSA-N 0.000 claims description 3
- KLERNTFVTLXLIO-VHSXEESVSA-N 2,6-dibromo-4-[[[(1s,3r)-3-hydroxycyclohexyl]amino]methyl]phenol Chemical compound C1[C@H](O)CCC[C@@H]1NCC1=CC(Br)=C(O)C(Br)=C1 KLERNTFVTLXLIO-VHSXEESVSA-N 0.000 claims description 3
- YHZLVKSVOXPSQJ-UHFFFAOYSA-N 2-(aminomethyl)-4,6-dibromophenol Chemical compound NCC1=CC(Br)=CC(Br)=C1O YHZLVKSVOXPSQJ-UHFFFAOYSA-N 0.000 claims description 3
- RVELKTSHKDTMSZ-UHFFFAOYSA-N 4-(bromomethyl)-2,6-dichlorophenol Chemical compound OC1=C(Cl)C=C(CBr)C=C1Cl RVELKTSHKDTMSZ-UHFFFAOYSA-N 0.000 claims description 3
- 150000001299 aldehydes Chemical class 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 239000004411 aluminium Substances 0.000 claims description 3
- 229910052782 aluminium Inorganic materials 0.000 claims description 3
- 238000011065 in-situ storage Methods 0.000 claims description 3
- 239000002798 polar solvent Substances 0.000 claims description 3
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 3
- GOBHPJAZGSDEPM-UHFFFAOYSA-N 3,5-dibromo-N-cyclohexyl-N-ethyl-2-hydroxybenzamide Chemical compound C(C)N(C(C1=C(C(=CC(=C1)Br)Br)O)=O)C1CCCCC1 GOBHPJAZGSDEPM-UHFFFAOYSA-N 0.000 claims description 2
- BXBJZYXQHHPVGO-UHFFFAOYSA-N 4-hydroxycyclohexan-1-one Chemical compound OC1CCC(=O)CC1 BXBJZYXQHHPVGO-UHFFFAOYSA-N 0.000 claims description 2
- OTMHNNLBPAZCKU-HAQNSBGRSA-N BrC=1C=C(C2=C(CN(CO2)[C@@H]2CC[C@H](CC2)O)C1)Br Chemical compound BrC=1C=C(C2=C(CN(CO2)[C@@H]2CC[C@H](CC2)O)C1)Br OTMHNNLBPAZCKU-HAQNSBGRSA-N 0.000 claims description 2
- ABKMDMBPYLXSEK-XYPYZODXSA-N C(C)(=O)OC1=C(C(=O)N[C@@H]2CC[C@H](CC2)O)C=C(C=C1Br)Br Chemical compound C(C)(=O)OC1=C(C(=O)N[C@@H]2CC[C@H](CC2)O)C=C(C=C1Br)Br ABKMDMBPYLXSEK-XYPYZODXSA-N 0.000 claims description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 2
- XZARCRKMTIIUJS-UHFFFAOYSA-N [2,4-dibromo-6-[[cyclohexyl(ethyl)amino]methyl]phenyl] acetate Chemical compound C(C)(=O)OC1=C(CN(C2CCCCC2)CC)C=C(C=C1Br)Br XZARCRKMTIIUJS-UHFFFAOYSA-N 0.000 claims description 2
- ZIVIGJMXRHEFEH-WDEREUQCSA-N [2,6-dibromo-4-[[(1S,3R)-3-hydroxycyclohexyl]carbamoyl]phenyl] acetate Chemical compound C(C)(=O)OC1=C(C=C(C(=O)N[C@@H]2C[C@@H](CCC2)O)C=C1Br)Br ZIVIGJMXRHEFEH-WDEREUQCSA-N 0.000 claims description 2
- OUXSMCJTWURJBJ-UHFFFAOYSA-N [Br].BrC1=C(C(=C(C=C1)O)Br)Br Chemical compound [Br].BrC1=C(C(=C(C=C1)O)Br)Br OUXSMCJTWURJBJ-UHFFFAOYSA-N 0.000 claims description 2
- TUCNEACPLKLKNU-UHFFFAOYSA-N acetyl Chemical group C[C]=O TUCNEACPLKLKNU-UHFFFAOYSA-N 0.000 claims description 2
- 230000029936 alkylation Effects 0.000 claims description 2
- 238000005804 alkylation reaction Methods 0.000 claims description 2
- 125000001118 alkylidene group Chemical group 0.000 claims description 2
- 239000011230 binding agent Substances 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- FNIATMYXUPOJRW-UHFFFAOYSA-N cyclohexylidene Chemical compound [C]1CCCCC1 FNIATMYXUPOJRW-UHFFFAOYSA-N 0.000 claims description 2
- 229910000039 hydrogen halide Inorganic materials 0.000 claims description 2
- 239000012433 hydrogen halide Substances 0.000 claims description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 2
- 229940071870 hydroiodic acid Drugs 0.000 claims description 2
- 239000011630 iodine Substances 0.000 claims description 2
- 150000002500 ions Chemical class 0.000 claims description 2
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical group [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 2
- 230000011987 methylation Effects 0.000 claims description 2
- 238000007069 methylation reaction Methods 0.000 claims description 2
- 150000002902 organometallic compounds Chemical class 0.000 claims description 2
- 229910052698 phosphorus Inorganic materials 0.000 claims description 2
- 239000011574 phosphorus Substances 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims 7
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims 7
- 230000001335 demethylating effect Effects 0.000 claims 4
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 3
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims 3
- 239000003638 chemical reducing agent Substances 0.000 claims 3
- WRCJXNZKBVBWRN-VZXYPILPSA-N (1R,3S)-3-[(3,5-dibromo-4-methoxyphenyl)methylamino]cyclohexan-1-ol hydrochloride Chemical compound Cl.BrC=1C=C(CN[C@@H]2C[C@@H](CCC2)O)C=C(C1OC)Br WRCJXNZKBVBWRN-VZXYPILPSA-N 0.000 claims 1
- WRCJXNZKBVBWRN-ACMTZBLWSA-N (1S,3S)-3-[(3,5-dibromo-4-methoxyphenyl)methylamino]cyclohexan-1-ol hydrochloride Chemical compound Cl.BrC=1C=C(CN[C@@H]2C[C@H](CCC2)O)C=C(C1OC)Br WRCJXNZKBVBWRN-ACMTZBLWSA-N 0.000 claims 1
- FYTGYFIHOPZTEL-UHFFFAOYSA-N 2,4-dibromo-6-[2-[2-(3,5-dibromo-2-hydroxyphenyl)ethoxy]ethyl]phenol Chemical compound BrC=1C(=C(CCOCCC2=C(C(=CC(=C2)Br)Br)O)C=C(C1)Br)O FYTGYFIHOPZTEL-UHFFFAOYSA-N 0.000 claims 1
- ANCYFYWRSWWXGE-ZJUUUORDSA-N 2,6-dibromo-4-[[(1R,3S)-3-hydroxycyclohexyl]iminomethyl]phenol Chemical compound C1[C@@H](O)CCC[C@H]1N=CC1=CC(Br)=C(O)C(Br)=C1 ANCYFYWRSWWXGE-ZJUUUORDSA-N 0.000 claims 1
- CLNYPAYJTBLRJL-DTWKUNHWSA-N 3,5-dibromo-4-hydroxy-N-[(1S,3R)-3-hydroxycyclohexyl]benzamide Chemical compound BrC=1C=C(C(=O)N[C@@H]2C[C@@H](CCC2)O)C=C(C1O)Br CLNYPAYJTBLRJL-DTWKUNHWSA-N 0.000 claims 1
- VBXCHSPLNZRAQX-WCQYABFASA-N 4-[[[(1S,3R)-3-hydroxycyclohexyl]amino]methyl]phenol Chemical compound C1[C@H](O)CCC[C@@H]1NCC1=CC=C(O)C=C1 VBXCHSPLNZRAQX-WCQYABFASA-N 0.000 claims 1
- ULYYFAJRDTXEMV-MCJVGQIASA-N 4-[[benzyl-[(1S,3R)-3-hydroxycyclohexyl]amino]methyl]-2,6-dibromophenol hydrochloride Chemical compound Cl.C(C1=CC=CC=C1)N([C@@H]1C[C@@H](CCC1)O)CC1=CC(=C(C(=C1)Br)O)Br ULYYFAJRDTXEMV-MCJVGQIASA-N 0.000 claims 1
- ULYYFAJRDTXEMV-QJHJCNPRSA-N 4-[[benzyl-[(1S,3S)-3-hydroxycyclohexyl]amino]methyl]-2,6-dibromophenol hydrochloride Chemical compound Cl.C(C1=CC=CC=C1)N([C@@H]1C[C@H](CCC1)O)CC1=CC(=C(C(=C1)Br)O)Br ULYYFAJRDTXEMV-QJHJCNPRSA-N 0.000 claims 1
- YICJEGQUGXZLGR-KYZUINATSA-N BrC=1C(=C(C(=O)N[C@@H]2CC[C@H](CC2)O)C=C(C1)Br)O Chemical compound BrC=1C(=C(C(=O)N[C@@H]2CC[C@H](CC2)O)C=C(C1)Br)O YICJEGQUGXZLGR-KYZUINATSA-N 0.000 claims 1
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 claims 1
- MKUPOLVOQKUHTE-IYARVYRRSA-N C(C1=CC=CC=C1)N([C@@H]1CC[C@H](CC1)O)CC1=C(C(=CC(=C1)Br)Br)O Chemical compound C(C1=CC=CC=C1)N([C@@H]1CC[C@H](CC1)O)CC1=C(C(=CC(=C1)Br)Br)O MKUPOLVOQKUHTE-IYARVYRRSA-N 0.000 claims 1
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- 150000003935 benzaldehydes Chemical class 0.000 description 1
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- 239000010941 cobalt Substances 0.000 description 1
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- 150000002367 halogens Chemical class 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- ATADHKWKHYVBTJ-UHFFFAOYSA-N hydron;4-[1-hydroxy-2-(methylamino)ethyl]benzene-1,2-diol;chloride Chemical compound Cl.CNCC(O)C1=CC=C(O)C(O)=C1 ATADHKWKHYVBTJ-UHFFFAOYSA-N 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- MJGFBOZCAJSGQW-UHFFFAOYSA-N mercury sodium Chemical compound [Na].[Hg] MJGFBOZCAJSGQW-UHFFFAOYSA-N 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
- GSSNBCHDTWIOLI-UHFFFAOYSA-N n-benzylpentan-1-amine Chemical compound CCCCCNCC1=CC=CC=C1 GSSNBCHDTWIOLI-UHFFFAOYSA-N 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 235000020030 perry Nutrition 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- OENLEHTYJXMVBG-UHFFFAOYSA-N pyridine;hydrate Chemical compound [OH-].C1=CC=[NH+]C=C1 OENLEHTYJXMVBG-UHFFFAOYSA-N 0.000 description 1
- 238000006268 reductive amination reaction Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- XIIOFHFUYBLOLW-UHFFFAOYSA-N selpercatinib Chemical compound OC(COC=1C=C(C=2N(C=1)N=CC=2C#N)C=1C=NC(=CC=1)N1CC2N(C(C1)C2)CC=1C=NC(=CC=1)OC)(C)C XIIOFHFUYBLOLW-UHFFFAOYSA-N 0.000 description 1
- 229910001023 sodium amalgam Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 239000002511 suppository base Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 150000003613 toluenes Chemical class 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/182—Radicals derived from carboxylic acids
- C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pulmonology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (10)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP2251891.8 | 1972-10-23 | ||
| DE19722251891 DE2251891C3 (de) | 1972-10-23 | Benzylamine, deren physiologisch verträglichen Salze, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel | |
| DEP2316325.9 | 1973-04-02 | ||
| DE2316325A DE2316325A1 (de) | 1972-10-23 | 1973-04-02 | Neue verfahren zur herstellung von benzylaminen |
| DEP2320967.8 | 1973-04-26 | ||
| DE19732320967 DE2320967C3 (de) | 1973-04-26 | Neue Benzylamine, deren physiologisch verträgliche Salze, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel | |
| DEP2337932.0 | 1973-07-26 | ||
| DE19732337932 DE2337932A1 (de) | 1972-10-23 | 1973-07-26 | Neue verfahren zur herstellung von benzylaminen |
| DE2346743A DE2346743C3 (de) | 1972-10-23 | 1973-09-17 | 2- oder 4-Hydroxy-3,5-dihalogenbenzylamine, deren physiologisch verträgliche Salze, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel |
| DEP2346743.8 | 1973-09-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1092113A true CA1092113A (en) | 1980-12-23 |
Family
ID=27510276
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA183,899A Expired CA1092113A (en) | 1972-10-23 | 1973-10-22 | Benzylamines |
Country Status (16)
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AT332863B (de) * | 1973-01-02 | 1976-10-25 | Gerot Pharmazeutika | Verfahren zur herstellung von neuen 2-aminomethyl-4,6-dihalogenphenolderivaten sowie deren additionssalzen mit sauren |
| WO1980000561A1 (fr) * | 1978-09-06 | 1980-04-03 | Sandoz Ag | Derives de l'(alpha)-alcoyle-o-oxy-benzylamine, leur preparation et remedes les contenant |
| US4578390A (en) * | 1981-12-14 | 1986-03-25 | Merck & Co., Inc. | Hydroxybenzylamino derivatives as anti-inflammatory agents |
| GB8606066D0 (en) * | 1986-03-12 | 1986-04-16 | Ici Plc | Bromine-containing polyols |
| DE3820292A1 (de) * | 1988-06-15 | 1990-04-12 | Basf Ag | Aminomethylphenole und diese enthaltende fungizide |
| EP2179651A4 (en) * | 2007-06-29 | 2012-07-11 | Sumitomo Chemical Co | MEANS FOR THE CONTROL OF PLANT DISEASES AND METHOD FOR THE CONTROL OF PLANT DISEASES |
| JP6683696B2 (ja) * | 2014-11-05 | 2020-04-22 | ダウ グローバル テクノロジーズ エルエルシー | 難燃性ポリオール |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB836934A (en) * | 1957-10-03 | 1960-06-09 | Monsanto Chemicals | Phenolic amino compounds |
-
1973
- 1973-10-16 NL NLAANVRAGE7314216,A patent/NL180978C/xx not_active IP Right Cessation
- 1973-10-19 FI FI3254/73A patent/FI62051C/fi active
- 1973-10-19 SU SU1963879A patent/SU530638A3/ru active
- 1973-10-22 CA CA183,899A patent/CA1092113A/en not_active Expired
- 1973-10-22 HU HUTO938A patent/HU168131B/hu unknown
- 1973-10-22 IE IE01888/73A patent/IE38961B1/xx unknown
- 1973-10-22 SE SE7314321A patent/SE409699B/sv unknown
- 1973-10-22 JP JP11886973A patent/JPS5535374B2/ja not_active Expired
- 1973-10-22 DK DK571973A patent/DK149883C/da active
- 1973-10-22 BE BE136949A patent/BE806375A/xx not_active IP Right Cessation
- 1973-10-22 NO NO4087/73A patent/NO138251C/no unknown
- 1973-10-23 FR FR7337753A patent/FR2203639B1/fr not_active Expired
- 1973-10-23 CH CH1147977A patent/CH605621A5/xx not_active IP Right Cessation
- 1973-10-23 CH CH1494973A patent/CH597148A5/xx not_active IP Right Cessation
- 1973-10-23 CH CH1147777A patent/CH611871A5/xx not_active IP Right Cessation
- 1973-10-23 CH CH1148077A patent/CH602573A5/xx not_active IP Right Cessation
- 1973-10-23 CH CH1147577A patent/CH602571A5/xx not_active IP Right Cessation
- 1973-10-23 CH CH1148377A patent/CH602575A5/xx not_active IP Right Cessation
- 1973-10-23 CH CH1148277A patent/CH603550A5/xx not_active IP Right Cessation
- 1973-10-23 CH CH1148177A patent/CH602574A5/xx not_active IP Right Cessation
- 1973-10-23 CH CH1147677A patent/CH605620A5/xx not_active IP Right Cessation
- 1973-10-23 DD DD174238A patent/DD108974A5/xx unknown
- 1973-10-23 CH CH1148477A patent/CH602576A5/xx not_active IP Right Cessation
- 1973-10-23 GB GB4933973A patent/GB1450702A/en not_active Expired
-
1975
- 1975-04-23 AT AT309675A patent/AT330149B/de not_active IP Right Cessation
-
1977
- 1977-09-20 CH CH1147877A patent/CH602572A5/xx not_active IP Right Cessation
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