SU482449A1 - The method of obtaining - (-phenylethyl) lactam - Google Patents

Description

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The invention relates to the field of production of - (| 3-phenylethyl) -lactams, in particular N- (| 3-phenylethyl) -pyrrolidone, piperidone and caprolactam, which are of interest as starting compounds in the synthesis of tricyclic isoquinolines and other substances that may be found application in the pharmaceutical industry.

A known method of producing analogous N- (p-phenylethyl) lactams from the corresponding phenacyl bromides by reacting them with piperidine, followed by reduction with sodium borohydride, oxidizing the intermediate alcohol with mercury salts and hydrogenating the oxazole derivative to the target products.

However, the known method is multi-stage, uses toxic and inaccessible raw materials, is not technological, and can not be used in production.

The same disadvantages have a method of obtaining N- (| 3-phenylethyl) -lactams, based on the use of styrene oxide and a-formyl-a-phenylacetic ester as a raw material.

A new simple and technologically advanced method for the preparation of N- (p-phenylethyl) lactams has been proposed, based on the use of available lactym esters.

The method for preparing N- (p-phenylethyl) -lactams is that the o-methyl lactime esters are reacted with p-phenylethyl alcohol at 70-200 ° C, followed by non-aggregation of the o- (p-phenylethyl) lactime effects that are formed heating in the presence of catalytic amounts of dimethyl sulfate and the selection of the target products by known methods Example 1. Preparation of o- (p-phenylethyl) butyrolactime

30 g (0.304 mol) of o-methylbutyrolactim and 37 g (0.304 mol) of p-phenylethyl alcohol are heated for 7 hours at 120 ° C with distillation of methanol (control by GLC) and distilled. Yield 19.3 g (34.2%); m.p. 108-110 ° С (1 mm of mercury); p 2.0 1.5235.

Found,%: C 76.33; H 7.96; N 7.28.

CizHisNO. Calculated,%: C 76.19; H 7.94; N 7.41.

Example 2. Getting o- (p-phenylethyl) -valerolactim.

Synthesized as in Example I; reaction temperature 150 ° C, reaction time 7 hours, yield 50%; m.p. 120 ° (1-2 mm of mercury.); n 4,531.

Found,%: C 76.87; H 8.42; N 6.81.

CisHirNO.

Calculated,%: C, 76.85; H 8.37; N 6.9.

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Example 3. Obtaining o- (p-phenylethyl) caprolactym. ,

Synthesized as in Example I; reaction temperature 140 ° C; reaction time is 7 hours; yield 48.5%; m.p. 124-126 ° C (1-2 mm of mercury.); N |, about 1.5275.

Found,%: C 77.72; H 8.75; N 6.57.

CnHigNO.

Calculated,%: C 77.42; H 8.75; N 6.45.

Example 4. Obtaining N- ((3-phenylethyl) -pyrrolidone-2.

19.3 g (0.102 mol) of o- (p-phenylethyl) -butyrolactim and 0.5 ml (0.0053 mol) of dimethyl sulfate are heated at 140-150 ° C for 3 hours (monitored by GLC), N-methylbutyrolactam is distilled off and distilled. Yield 11.2 g (58%); m.p. 135-150 ° С (1-2 mm of mercury); m.p. 53-54 ° C (from petroleum ether).

Found,%: C 76.24; H 8.00; N 7.27.

Ci2Hi5NO.

Calculated,%: C 76.19; H 7.94; N 7.41.

Example 5. Obtaining N- (p-phenylethyl) -piperidone-2.

Synthesized as in Example 4; reaction temperature 170-180 ° C; yield 43%;

20

156-158 ° C (1-2 mm of mercury.); P

m.p. 1.5455.

Found,%: C 76.72; H 8.16; N 6.81.

CisHirNO.

Calculated,%: C, 76.85; H 8.37; N 6.9.

Example 6. Obtaining N- (p-phenylethyl) -caprolactime.

Synthesized as in Example 4; reaction temperature 170-180 ° C; reaction time 3 hours; yield 48.8%; m.p. 150-165 ° C (1 - 2 mm Hg. Art.); m.p. 40-42 ° C (from petroleum ether).

Found,%: C 77.68; H 8.74; N 6.08.

CuHjgNO.

Calculated,%: C 77.42; H 8.74; N 6.45.

Subject invention

The method of obtaining N- (p-phenylethyl) -lactams, characterized in that, in order to simplify the process and expand the raw material base,

o-methyl lactime esters are reacted with p-phenethyl alcohol at a temperature of 70-200 ° C, followed by rearrangement of the o (rphenylethyl) -lactable esters resulting from this with heating B in the presence of catalytic amounts

dimethyl sulfate and the selection of target products by known methods.