Methanesulfonyl chloride → 8-chloro-10(11H)-[1-(phenylmethyl)-4-piperidinylmethyl]dibenz[b,f][1,4]thiazepine

HRID 1707652Notes

Reaction equation

HRID 1707652 reaction equation
C(O[C:4]([CH:6]1[CH2:11][CH2:10][N:9]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:8][CH2:7]1)=O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].CS([O-])(=O)=O.CS(Cl)(=O)=O.[Cl:35][C:36]1[CH:50]=[CH:49][C:39]2[S:40][C:41]3[CH:48]=[CH:47][CH:46]=[CH:45][C:42]=3[CH2:43][NH:44][C:38]=2[CH:37]=1.C(N(C(C)C)CC)(C)C>C1COCC1.C1(C)C=CC=CC=1>[Cl:35][C:36]1[CH:50]=[CH:49][C:39]2[S:40][C:41]3[CH:48]=[CH:47][CH:46]=[CH:45][C:42]=3[CH2:43][N:44]([CH2:4][CH:6]3[CH2:7][CH2:8][N:9]([CH2:12][C:13]4[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=4)[CH2:10][CH2:11]3)[C:38]=2[CH:37]=1

Participants

9

Reactant 6

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 85257MethanesulfonateHCID 90423Ethyl 1-benzylpiperidine-4-carboxylateHCID 21226445Aluminium lithium hydrideHCID 542201108-Chloro-10,11-dihydrodibenzo[b,f][1,4]thiazepine

Product 1

HCID 193775958-chloro-10(11H)-[1-(phenylmethyl)-4-piperidinylmethyl]dibenz[b,f][1,4]thiazepine

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A sample of 1-benzylpiperidine-4-carboxylic acid ethyl ester is reduced to 1-benzylpiperidine-4-hydroxymethyl by treatment with lithium aluminum hydride (LiAlH4) in THF. This material is converted to its methane sulfonate by reaction with methanesulfonyl chloride. This material, 1-benzylpiperidine-4-methylmethane sulfonate, the product of Example 104, and diisopropylethyl amine are refluxed in toluene the provide the title compound.

Sources & evidence

ORD record
ord-9f59871417ef4721ba9b8935e4e85f62
Source dataset
uspto-grants-1994_10
Patent number
US05354747

Reaction notes

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