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

HRID 377814Notes

Reaction equation

HRID 377814 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

5

Reactant 3

HCID 11430Potassium CarbonateHCID 118127101-Benzoyl-3-(3,4-dichlorophenyl)-3-[3-(methanesulfonyloxy)propyl]piperidineHCID 227417544-Amino-4-phenylpiperidine dibenzenesulfonate

Product 1

HCID 152855913-[3-(4-Amino-4-phenylpiperid-1-yl)propyl]-1-benzoyl-3-(3,4-dichlorophenyl)-piperidineYield 59.2%

Reagents, catalysts & solvents 1

HCID 21891449acetonitrile N,N-dimethylformamideSolvent

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 1 00° 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

  1. temperatureis heated at 1 00° C
  2. concentrationIt is concentrated under vacuum
  3. extractionextracted with AcOEt
  4. washthe organic phase is washed with water and with saturated NaCl solution
  5. dry with materialdried over MgSO4
  6. customthe solvent is evaporated off under vacuum
  7. customThe residue is chromatographed on silica H

Sources & evidence

ORD record
ord-ab2da7205e334c62b8979d8e29d1daee
Source dataset
uspto-grants-2000_02
Patent number
US06028082

Reaction notes

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