Potassium Carbonate → 3-[3-(4-Amino-4-phenylpiperid-1-yl)propyl]-1-benzoyl-3-(3,4-dichlorophenyl)-piperidine

HRID 1597094Notes

Reaction equation

C1(S(O)(=O)=O)C=CC=CC=1.C1(S(O)(=O)=O)C=CC=CC=1.[NH2:21][C:22]1([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1.[C:34]([N:42]1[CH2:47][CH2:46][CH2:45][C:44]([C:56]2[CH:61]=[CH:60][C:59]([Cl:62])=[C:58]([Cl:63])[CH:57]=2)([CH2:48][CH2:49][CH2:50]OS(C)(=O)=O)[CH2:43]1)(=[O:41])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.C(#N)C>[NH2:21][C:22]1([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:27][CH2:26][N:25]([CH2:50][CH2:49][CH2:48][C:44]2([C:56]3[CH:61]=[CH:60][C:59]([Cl:62])=[C:58]([Cl:63])[CH:57]=3)[CH2:45][CH2:46][CH2:47][N:42]([C:34](=[O:41])[C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[CH2:43]2)[CH2:24][CH2:23]1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 6.81 g of 4-amino-4-phenylpiperidine dibenzenesulfonate, 5.2 g of the compound obtained in step B of EXAMPLE 1 and 6.1 g of K2CO3 in 30 ml of a DMF/acetonitrile mixture (50/50; v/v) is heated at 100° C. for 5 hours. It is concentrated under vacuum, the residue is taken up with water and extracted with AcOEt, the organic phase is washed with water and with saturated NaCl solution and dried over MgSO4 and the solvent is evaporated off under vacuum. The residue is chromatographed on silica H using a DCM/MeOH mixture (from 99/1; v/v to 85/15; v/v) as the eluent to give 3.6 g of the expected product.

Workup

concentrationIt is concentrated under vacuum
extractionextracted with AcOEt
washthe organic phase is washed with water and with saturated NaCl solution
dry with materialdried over MgSO4
customthe solvent is evaporated off under vacuum
customThe residue is chromatographed on silica H

Sources & evidence

ORD record: ord-857efcdcda5a48a29602cd1ec137f25e
Source dataset: uspto-grants-2001_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06291672B1

Reaction notes

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