Sodium Bicarbonate → HCID 22396241, compound

HRID 1070523

Reaction equation

HRID 1070523 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][C:15]=1[Cl:16])[CH2:5][N:6]1[CH2:11][CH2:10][CH:9]([NH2:12])[CH2:8][CH2:7]1.[N:17]1[CH:22]=[CH:21][CH:20]=[C:19]([CH2:23][CH2:24][CH:25]=O)[CH:18]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>ClCCl.O.C(O)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][C:15]=1[Cl:16])[CH2:5][N:6]1[CH2:7][CH2:8][CH:9]([NH:12][CH2:25][CH2:24][CH2:23][C:19]2[CH:18]=[N:17][CH:22]=[CH:21][CH:20]=2)[CH2:10][CH2:11]1

Participants

8

Reactant 4

HCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 109781561-[(3,4-Dichlorophenyl)methyl]piperidin-4-amineHCID 111054123-(Pyridin-3-yl)propanal

Product 1

HCID 22396241HCID 22396241, compoundYield 25.6%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared from 1-(3,4-dichlorobenzyl)piperidine-4-amine (free base 187 mg), 3-(3-pyridinyl)propanal (125 mg), sodium triacetoxyborohydride (70 mg), and 0.02 ml acetic acid, stirred together for 2 hrs in dichloromethane (10 ml). Water was added, the mixture neutralised with sodium bicarbonate and the organic phase separated, dried and chromatographed on silica with ethyl acetate/methanol (9:1) as eluant, to give the title compound (70 mg) as a colourless oil.

Workup

  1. customthe organic phase separated
  2. customdried
  3. customchromatographed on silica with ethyl acetate/methanol (9:1) as eluant

Sources & evidence

ORD record
ord-f839854a165b477ba9793d28761d34e6
Source dataset
uspto-grants-2005_06
Patent number
US06903085B1

Linked notes

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