JP4478827B2 - アミンボランを用いるアミンの製造方法 - Google Patents
アミンボランを用いるアミンの製造方法 Download PDFInfo
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- JP4478827B2 JP4478827B2 JP2003436391A JP2003436391A JP4478827B2 JP 4478827 B2 JP4478827 B2 JP 4478827B2 JP 2003436391 A JP2003436391 A JP 2003436391A JP 2003436391 A JP2003436391 A JP 2003436391A JP 4478827 B2 JP4478827 B2 JP 4478827B2
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- 150000001412 amines Chemical class 0.000 title claims description 21
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 title claims description 15
- 229910000085 borane Inorganic materials 0.000 title claims description 12
- 238000004519 manufacturing process Methods 0.000 title claims description 9
- 239000002904 solvent Substances 0.000 claims description 21
- 150000002466 imines Chemical class 0.000 claims description 10
- QHXLIQMGIGEHJP-UHFFFAOYSA-N boron;2-methylpyridine Chemical compound [B].CC1=CC=CC=N1 QHXLIQMGIGEHJP-UHFFFAOYSA-N 0.000 claims description 9
- -1 amine boranes Chemical class 0.000 claims description 8
- NNTOJPXOCKCMKR-UHFFFAOYSA-N boron;pyridine Chemical compound [B].C1=CC=NC=C1 NNTOJPXOCKCMKR-UHFFFAOYSA-N 0.000 claims description 7
- 150000001728 carbonyl compounds Chemical class 0.000 claims description 7
- 239000003638 chemical reducing agent Substances 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 5
- WVMHLYQJPRXKLC-UHFFFAOYSA-N borane;n,n-dimethylmethanamine Chemical compound B.CN(C)C WVMHLYQJPRXKLC-UHFFFAOYSA-N 0.000 claims description 3
- YJROYUJAFGZMJA-UHFFFAOYSA-N boron;morpholine Chemical compound [B].C1COCCN1 YJROYUJAFGZMJA-UHFFFAOYSA-N 0.000 claims description 3
- 150000003335 secondary amines Chemical class 0.000 claims description 3
- YPWBYWNNJVSNPQ-UHFFFAOYSA-N borane;n,n-diethylaniline Chemical compound B.CCN(CC)C1=CC=CC=C1 YPWBYWNNJVSNPQ-UHFFFAOYSA-N 0.000 claims description 2
- 150000003141 primary amines Chemical class 0.000 claims description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 31
- 238000006243 chemical reaction Methods 0.000 description 27
- 239000011734 sodium Substances 0.000 description 17
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 16
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 15
- 238000006268 reductive amination reaction Methods 0.000 description 15
- 239000000243 solution Substances 0.000 description 14
- 239000000203 mixture Substances 0.000 description 13
- 238000001816 cooling Methods 0.000 description 11
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 10
- 239000003960 organic solvent Substances 0.000 description 10
- 229910052786 argon Inorganic materials 0.000 description 8
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 8
- 239000010410 layer Substances 0.000 description 8
- 239000012044 organic layer Substances 0.000 description 8
- 230000002829 reductive effect Effects 0.000 description 8
- 238000010898 silica gel chromatography Methods 0.000 description 8
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 8
- ZMASBEFBIXMNCP-UHFFFAOYSA-N borane;2-methylpyridine Chemical compound B.CC1=CC=CC=N1 ZMASBEFBIXMNCP-UHFFFAOYSA-N 0.000 description 7
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 6
- 238000002451 electron ionisation mass spectrometry Methods 0.000 description 6
- 239000011259 mixed solution Substances 0.000 description 6
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 5
- 238000006722 reduction reaction Methods 0.000 description 5
- 239000002262 Schiff base Substances 0.000 description 4
- 150000004753 Schiff bases Chemical class 0.000 description 4
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 4
- RJTANRZEWTUVMA-UHFFFAOYSA-N boron;n-methylmethanamine Chemical compound [B].CNC RJTANRZEWTUVMA-UHFFFAOYSA-N 0.000 description 4
- 125000000753 cycloalkyl group Chemical group 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- BVAUMRCGVHUWOZ-ZETCQYMHSA-N (2s)-2-(cyclohexylazaniumyl)propanoate Chemical compound OC(=O)[C@H](C)NC1CCCCC1 BVAUMRCGVHUWOZ-ZETCQYMHSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 150000008365 aromatic ketones Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 239000002198 insoluble material Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 2
- 239000012321 sodium triacetoxyborohydride Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- GFEPEQYRZIPEIX-UHFFFAOYSA-N 1-(2-aminophenyl)-2-phenylethane-1,2-dione Chemical compound NC1=CC=CC=C1C(=O)C(=O)C1=CC=CC=C1 GFEPEQYRZIPEIX-UHFFFAOYSA-N 0.000 description 1
- CWEGCQIIDCZZED-UHFFFAOYSA-N 1-benzylpyrrolidine Chemical compound C=1C=CC=CC=1CN1CCCC1 CWEGCQIIDCZZED-UHFFFAOYSA-N 0.000 description 1
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- XNNKQIPMIAMBJO-UHFFFAOYSA-N aniline;boron Chemical compound [B].NC1=CC=CC=C1 XNNKQIPMIAMBJO-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 238000004896 high resolution mass spectrometry Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- IUERBKSXAYWVGE-UHFFFAOYSA-N n-(1-phenylethyl)aniline Chemical compound C=1C=CC=CC=1C(C)NC1=CC=CC=C1 IUERBKSXAYWVGE-UHFFFAOYSA-N 0.000 description 1
- FALTVGCCGMDSNZ-UHFFFAOYSA-N n-(1-phenylethyl)benzamide Chemical compound C=1C=CC=CC=1C(C)NC(=O)C1=CC=CC=C1 FALTVGCCGMDSNZ-UHFFFAOYSA-N 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
本発明は、安定で取り扱い易い還元剤であるアミンボランを用いて、イミンからアミンを無溶媒で製造する還元方法を提供することを目的とする。
Cyclohexanone(3.000g,30.57mmol),aniline(2.847g,30.57mmol)の混合溶液に、氷冷攪拌下、picoline−borane(3.270g,30.57mmol)を約10分かけて加えた後、室温に戻し、argon気流下10時間撹拌した。反応終了後、反応溶液に10%Na2CO3(50mL)を加え、水層をAcOEt(75mL x2)で抽出し、有機層を合わせて飽和食塩水(30mL)で洗浄し、Na2SO4で乾燥した。有機溶媒を減圧留去し、残渣をシリカゲルカラムクロマトグラフィー(展開溶媒:AcOEt−Hexane=1:3)に付し、N−cyclohexylaniline(4.363g,81.4%)を得た。
1H NMR(DMSO−d6)δ;1.05−2.12(m,10H,CH2x5),3.07−3.23(m,1H,CH),5.35(s,1H,NH),6.46(t,J=7.2Hz,1H,ArH),6.54(d,J=7.8Hz,2H,ArH),7.02(t,J=7.8Hz,2H,ArH)
EI−MS m/z;175(M+,41.27),132(100)
AcOH(0.5mL)を加え,反応時間を3.5時間にする以外は実施例1と全く同じ条件下反応を行いN−cyclohexylaniline(5.054g,94.3%)を得た。
Benzaldehyde(830mg,7.82mmol),pyrrolidine(1669mg,23.47mmol)の混合溶液に、氷冷下、AcOH(0.3mL)を加え、picoline−borane(837mg,7.83mmol)を約5分かけて加えた後、室温に戻し、argon気流下10時間撹拌した。反応終了後、反応溶液に10%HCl(10mL)を加え、室温で30分撹拌した。反応溶液に、氷冷下、Na2CO3(約2.5g)を加えてアルカリ性とし、さらにH2O(10mL)を加え、水層をAcOEt(30mL x2)で抽出し、有機層を合わせて飽和食塩水(15mL)で洗浄し、Na2SO4で乾燥した。有機溶媒を減圧留去し、残渣をシリカゲルカラムクロマトグラフィー(展開溶媒:AcOEt)に付し、N−benzylpyrrolidine(961mg,76.2%)を得た。
1H NMR(CDCl3,270MHz)δ;1.70−1.87(m,4H,CH2 x2),2.43−2.58(m,4H,CH2 x2),3.61(s,2H,CH2),7.19−7.36(m,5H,ArH)
13C NMR(CDCl3,67.8MHz);23.59,54.12,60.71,126.81,128.15,128.87,139.28
EI−MS m/z;161(M+,34.21),91(100)
HR−MS m/z;for C11H15N calcd 161.1204,found 161.1205
Acotophenone(1.000g,8.32mmol),aniline(0.775g,8.32mmol),AcOH(0.3mL)の混合溶液にpicoline−borane(0.890g,8.32mmol)を約5分かけて加え、argon気流下、室温で63.5時間撹拌した。反応終了後、反応溶液に10%HCl(10mL)を加え、室温で30分撹拌した。反応溶液に、氷冷下、Na2CO3(約2.5g)を加えてアルカリ性とし、さらにH2O(10mL)を加え、水層をAcOEt(30mL x2)で抽出し、有機層を合わせて飽和食塩水(15mL)で洗浄し、Na2SO4で乾燥した。有機溶媒を減圧留去し、残渣をシリカゲルカラムクロマトグラフィー(展開溶媒:AcOEt−Hexane=1:3)に付し、N−phenyl−1−phenethylamine(1.498g,91.2%)を得た。
1H NMR(CDCl3,270MHz)δ;1.51(d,J=6.8Hz,3H,CH3),4.02(s,1H,NH),4.48(q,J=6.7Hz,1H,CH),6.51(dd,J=7.7,0.9Hz,2H,ArH),6.64(td,J=7.3,1.0Hz,1H,ArH),7.08(t,J=7.6Hz,2H,ArH),7.17−7.48(m,5H,ArH)
EI−MS m/z;197(M+,56.55),182(100),120(9.79),105(74.51),77(35.24).
Acotophenone(1.000g,8.32mmol),benzylamine(0.892g,8.32mmol),AcOH(0.3mL)の混合溶液にpicoline−borane(0.890g,8.32mmol)を約5分かけて加え、argon気流下、室温で72時間撹拌した。反応終了後、反応溶液に10%HCl(10mL)を加え、室温で30分撹拌した。反応溶液に、氷冷下、Na2CO3(約2.5g)を加えてアルカリ性とし、さらにH2O(10mL)を加え、水層をAcOEt(30mL x2)で抽出し、有機層を合わせて飽和食塩水(15mL)で洗浄し、Na2SO4で乾燥した。有機溶媒を減圧留去し、残渣をシリカゲルカラムクロマトグラフィー(展開溶媒:AcOEt−Hcxane=1:3)に付し、N−benzyl−1−phenethylamine(1.534g,87.2%)を得た。
1H NMR(CDCl3,270MHz)δ;1.37(d,J=6.6Hz,3H,CH3),3.59(d,J=13.3Hz,1H,CH2),3.67(d,J=13.3Hz,1H,CH2)[3.63(ABq,J=13.3Hz,2H,CH2)],3.81(q,J=6.7Hz,1H,CH),7.19−7.39(m,10H,ArH)
EI−MS m/z;211(M+,2.58),196(100),105(11.99)91(68.96).
4−Methyl−2−pentanone(1.000g,9.98mmol),benzylamine(1.070g,9.99mmol)の混合溶液に氷冷下、AcOH(0.2mL)を加えpicoline−borane(1.068g,9.99mmol)を約5分かけて加えた後、室温に戻しargon気流下3.5時間撹拌した。反応終了後、反応溶液に10%HCl(10mL)を加え、室温で30分撹拌した。反応溶液に、氷冷下、Na2CO3(約2.5g)を加えてアルカリ性とし、さらにH2O(10mL)を加え、水層をAcOEt(30mL x2)で抽出し、有機層を合わせて飽和食塩水(15mL)で洗浄し、Na2SO4で乾燥した。有機溶媒を減圧留去し、残渣をシリカゲルカラムクロマトグラフィー(展開溶媒:AcOEt−Hexane=1:2)に付し、N−(1,3−dimethylbutyl)benzylamine(1.212g,63.5%)を得た。
1H NMR(CDCl3,270MHz)δ;0.86(dd,J=6.5,1.7Hz,6H,CH3 x2),1.07(d,J=6.1Hz,3H,3H3),1.10−1.24(m,1H,CH2),1.31−1.44(m,1H,CH2),1.52(s,1H,NH),1.58−1.75(m,1H,CH),2.66−2.82(m,1H,CH),3.72(d,J=12.9Hz,1H,CH2),3.84(d,J=12.9Hz,1H,CH2)[3.78(ABq,J=12.9Hz,2H,CH2)],7.18−7.38(m,5H,ArH)
EI−MS m/z191(M+,0.95),91(100)
Cyclohexanone(3.000g,30.57mmol),aniline(2.847g,30.57mmol)の混合溶液に氷冷下、AcOH(0.5mL)を加えpicoline−borane(3.270g,30.57mmol)を約10分かけて加えた後、室温に戻しargon気流下3.5時間撹拌した。反応終了後、反応溶液に10%Na2CO3(50mL)を加えてアルカリ性とし、水層をAcOEt(75mL x2)で抽出し、有機層を合わせて飽和食塩水(30mL)で洗浄し、Na2SO4で乾燥した。有機溶媒を減圧留去し、残渣をシリカゲルカラムクロマトグラフィー(展開溶媒:AcOEt−Hexane=1:5)に付し、N−cyclohexylaniline(5.054g,94.3%)を得た。
1H NMR(DMSO−d6)δ;1.05−2.12(m,10H,CH2x5),3.07−3.23(m,1H,CH),5.35(S,1H,NH),6.46(t,J=7.2Hz,1H,ArH),6.54(d,J=7.8Hz,2H,ArH),7.02(t,J=7.8Hz,2H,ArH)
EI−MS m/z;175(M+,41.27),132(100)
Cyclohexanone(1.000g,10.19mmol),aniline(0.949g,10.19mmol)の混合溶液に氷冷下、AcOH(0.3mL)を加えpyridine−borane(0.947g,10.19mmol)を約3分かけて加えた後、室温に戻しargon気流下4時間撹拌した。反応終了後、反応溶液に10%HCl(10mL)を加えると不溶物が析出したので、AcOEt(4mL)を加え、そのまま室温で30分撹拌した。反応溶液に、氷冷下、10%Na2CO3(10mL)及びNa2CO3(約1.5g)を順に加えてアルカリ性とし、さらにH2O(4mL)を加え、水層をAcOEt(30mL x2)で抽出し、有機層を合わせて飽和食塩水(20mL)で洗浄し、Na2SO4で乾燥した。有機溶媒を減圧留去し、残渣をシリカゲルカラムクロマトグラフィー(AcOEt)に付し、N−cyclohexylaniline(1.758g,98.4%)を得た。
Cyclohexanone(1.000g,10.19mmol),aniline(0.949g,10.19mmol)の混合溶液に氷冷下、AcOH(0.3mL)を加えdimethylamine−borane(0.600g,10.18mmol)を約5分かけて加えた後、室温に戻しargon気流下22時間撹拌した。反応終了後、反応溶液に10%HCl(10mL)を加えると不溶物が析出したので、AcOEt(4mL)を加え、そのまま室温で30分撹拌した。反応溶液に、氷冷下、10%Na2CO3(10mL)及びNa2CO3(約1.5g)を順に加えてアルカリ性とし、さらにH2O(4mL)を加え、水層をAcOEt(30mL x2)で抽出し、有機層を合わせて飽和食塩水(20mL)で洗浄し、Na2SO4で乾燥した。有機溶媒を減圧留去し、残渣をシリカゲルカラムクロマトグラフィー(AcOEt−Hexane=1:3)に付し、N−cyclohexylaniline(0.874g,48.9%)及び原料のaniline(0.433g,45.6%)を得た。
Claims (1)
- 第一アミン又は第二アミンとカルボニル化合物から生成するイミン又はイミニウム化合物を還元してアミンを製造するにあたり、無溶媒で、かつ還元剤としてピコリンボラン、ピリジンボラン、モルホリンボラン、ジエチルアニリンボラン、ジメチルアミンボラン、トリメチルアミンボランから選択される一つ以上のアミンボランを用いることを特徴とするアミンの製造法。
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