Benzyl mercaptan → 4-[8-Chloro-5,6-Dihydro-4-(Phenylmethylthio)-11H-Benzo[5,6]Cyclohepta[1,2-b]Pyridin-11-Ylidene]-1-(3-Pyridinylacetyl)-Piperidine

HRID 840277Notes

Reaction equation

HRID 840277 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[C:8](=[C:18]3[CH2:23][CH2:22][N:21]([C:24](=[O:32])[CH2:25][C:26]4[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=4)[CH2:20][CH2:19]3)[C:9]3[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:10]=3[CH2:11][CH2:12][C:3]=12.[H-].[Na+].[CH2:35]([SH:42])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1>CN(C=O)C>[Cl:17][C:14]1[CH:15]=[CH:16][C:9]2[C:8](=[C:18]3[CH2:23][CH2:22][N:21]([C:24](=[O:32])[CH2:25][C:26]4[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=4)[CH2:20][CH2:19]3)[C:4]3=[N:5][CH:6]=[CH:7][C:2]([S:42][CH2:35][C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=4)=[C:3]3[CH2:12][CH2:11][C:10]=2[CH:13]=1

Participants

5

Reactant 3

HCID 7509Benzyl mercaptanHCID 24758Sodium hydrideHCID 226219554-[4,8-Dichloro-5,6-Dihydro-11H-Benzo[5,6]Cyclohepta[1,2-b]Pyridin-11-Ylidene]-1-(3-Pyridinylacetyl)-Piperidine

Product 1

HCID 226219804-[8-Chloro-5,6-Dihydro-4-(Phenylmethylthio)-11H-Benzo[5,6]Cyclohepta[1,2-b]Pyridin-11-Ylidene]-1-(3-Pyridinylacetyl)-PiperidineYield 8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of the title compound from Example 250 (0.25 grams), sodium hydride (0.11 grams, 60% in mineral oil), benzyl mercaptan (0.13 mL) and anhydrous DMF (15 mL) was stirred while being irradiated with a 200 W lamp for 10 days. Isolation and purification as in Example 257 provided the title compound (0.02 grams, 8%, MH+ 552).

Workup

  1. customwhile being irradiated with a 200 W lamp for 10 days
  2. customIsolation and purification as in Example 257

Sources & evidence

ORD record
ord-c4292c3538224eb8b9f4694bf54061e0
Source dataset
uspto-grants-2002_04
Patent number
US06365588B1

Reaction notes

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