4-(4-Chlorophenyl)-4-hydroxypiperidine → 37743-37-6

HRID 1368332Notes

Reaction equation

HRID 1368332 reaction equation
[Cl:1][CH2:2][CH2:3][C:4]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:5]([NH:7][CH3:8])=[O:6].[Cl:21][C:22]1[CH:27]=[CH:26][C:25]([C:28]2([OH:34])[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]2)=[CH:24][CH:23]=1>C(C(C)=O)C(C)C>[ClH:1].[Cl:21][C:22]1[CH:27]=[CH:26][C:25]([C:28]2([OH:34])[CH2:29][CH2:30][N:31]([CH2:2][CH2:3][C:4]([C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)([C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:5]([NH:7][CH3:8])=[O:6])[CH2:32][CH2:33]2)=[CH:24][CH:23]=1

Participants

4

Reactant 2

HCID 382824-(4-Chlorophenyl)-4-hydroxypiperidineHCID 18520143HCID 18520143, compound

Product 1

HCID 980594337743-37-6Yield 35%

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

A suspension of 4-chloro-N-methyl-2,2-diphenylbutyramide (1.4 g, 0.005 mol), 4-p-chlorophenyl-4-piperidinol (2.12 g, 0.01 mol), and trace Kl in i-BuCOMe (50 ml) was refluxed for 12 hrs. The reaction mixture was worked-up as described in Example 16 to provide 4-(p-chlorophenyl)-4-hydroxy-N-methyl-α,α-diphenyl-1-piperidinebutyramide hydrochloride (0.8 g, 35%), mp 236-238° C.

Workup

  1. temperaturewas refluxed for 12 hrs

Sources & evidence

ORD record
ord-363421b8dde54f9db96d12e871bba944
Source dataset
uspto-grants-2003_06
Patent number
US06573282B1

Reaction notes

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