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

HRID 50073

反応式

HRID 50073 の反応式
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.Cl.[C:35]([N:43]1[CH2:48][CH2:47][CH2:46][C:45]([C:65]2[CH:70]=[CH:69][C:68]([Cl:71])=[C:67]([Cl:72])[CH:66]=2)([CH2:49][CH2:50][CH2:51]N2CCC(C(N3CCCC3)=O)CC2)[CH2:44]1)(=[O:42])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=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]([CH2:51][CH2:50][CH2:49][C:45]2([C:65]3[CH:70]=[CH:69][C:68]([Cl:71])=[C:67]([Cl:72])[CH:66]=3)[CH2:46][CH2:47][CH2:48][N:43]([C:35](=[O:42])[C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[CH2:44]2)[CH2:24][CH2:23]1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 227417141-Benzoyl-3-(3,4-dichlorophenyl)-3-[3-[4-(pyrrolidin-1-ylcarbonyl)piperid-1-yl]propyl]piperidine hydrochlorideHCID 227417544-Amino-4-phenylpiperidine dibenzenesulfonate

生成物 1

HCID 152855913-[3-(4-Amino-4-phenylpiperid-1-yl)propyl]-1-benzoyl-3-(3,4-dichlorophenyl)-piperidine収率 74.6%

試薬・触媒・溶媒 1

HCID 21891449acetonitrile N,N-dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-7452e02e40fe423e8265ad2b71445983
出典データセット
uspto-grants-2004_03
特許番号
US06710042B2

関連ノート

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