2-Vinylpyridine → (S)-5,11-Dihydro-5-[1-(2-[2-pyridyl]ethyl)-2-pyrrolidinylmethyl]dibenzo[b,e][1,4]thiazepine

HRID 1460479Notes

Reaction equation

HRID 1460479 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=1)=[CH2:2].[NH:9]1[CH2:13][CH2:12][CH2:11][C@H:10]1[CH2:14][N:15]1[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=2[CH2:19][S:18][C:17]2[CH:26]=[CH:27][CH:28]=[CH:29][C:16]1=2>>[N:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[CH2:1][CH2:2][N:9]1[CH2:13][CH2:12][CH2:11][C@H:10]1[CH2:14][N:15]1[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=2[CH2:19][S:18][C:17]2[CH:26]=[CH:27][CH:28]=[CH:29][C:16]1=2

Participants

3

Reactant 2

HCID 75212-VinylpyridineHCID 22841647(S)-5,11-Dihydro-5-(2-pyrrolidinylmethyl)dibenzo[b,e][1,4]-thiazepine

Product 1

HCID 53971647(S)-5,11-Dihydro-5-[1-(2-[2-pyridyl]ethyl)-2-pyrrolidinylmethyl]dibenzo[b,e][1,4]thiazepineYield 58.3%

Conditions

Temperature
120 °C

Procedure

A mixture of 2-vinylpyridine (250 mg) and (S)-5,11-dihydro-5-(2-pyrrolidinylmethyl)dibenzo[b,e][1,4]thiazepine (see Preparations 13 and 14) (166 mg) was heated at 120° C. for 2 hours, cooled to room temperature and purified by chromatography on silica gel using ethyl acetate/methanol (10:1) as eluant. Appropriate fractions were combined and evaporated under reduced pressure to give the title compound as a pale brown gum, (131 mg, 58%).

Workup

  1. temperaturecooled to room temperature
  2. custompurified by chromatography on silica gel
  3. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-d590480b36894e7da85ba02f9b2180b9
Source dataset
uspto-grants-1991_12
Patent number
US05071844

Reaction notes

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