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

HRID 50073

Reaktionsgleichung

Reaktionsgleichung von HRID 50073
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

Komponenten

5

Edukt 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

Produkt 1

HCID 152855913-[3-(4-Amino-4-phenylpiperid-1-yl)propyl]-1-benzoyl-3-(3,4-dichlorophenyl)-piperidineAusbeute 74,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21891449acetonitrile N,N-dimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-7452e02e40fe423e8265ad2b71445983
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06710042B2

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