Ammonium Chloride → HCID 68471146, compound

HRID 2235313Notes

Reaction equation

HRID 2235313 reaction equation
[Cl:1][C:2]1[CH:21]=[C:20]([C:22]2[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=2)[CH:19]=[CH:18][C:3]=1[CH2:4][C:5]1([CH3:17])[CH2:9][CH2:8][N:7]([CH:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)[C:6]1=[O:16].[Cl-].[NH4+]>CO>[Cl-:1].[NH4+:7].[Cl:1][C:2]1[CH:21]=[C:20]([C:22]2[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=2)[CH:19]=[CH:18][C:3]=1[CH2:4][C:5]1([CH3:17])[CH2:9][CH2:8][N:7]([CH:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)[C:6]1=[O:16]

Participants

4

Reactant 2

HCID 25517Ammonium ChlorideHCID 59299409HCID 59299409, compound

Product 1

HCID 68471146HCID 68471146, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Free the bases in the mixture of 3-(2-chloro-4-pyridin-3-yl-benzyl)-1-cyclohexyl-3-methyl-pyrrolidin-2-one and 3-[1-(2-chloro-4-pyridin-3-yl-phenyl)-ethyl]-1-cyclohexyl-pyrrolidin-2-one, isomer 1 trifluoroacetic acid salts by passage through an SCX column eluting with methanol followed by 1N ammonia in methanol and evaporate. Further purify the residue by chromatography on silica gel (eluting with 15% acetonitrile in dichloromethane) to give first 3-[1-(2-chloro-4-pyridin-3-yl-phenyl)-ethyl]-1-cyclohexyl-pyrrolidin-2-one, isomer 1 (40 mg, 13%), and second 3-(2-chloro-4-pyridin-3-yl-benzyl)-1-cyclohexyl-3-methyl-pyrrolidin-2-one. To a solution of 3-(2-chloro-4-pyridin-3-yl-benzyl)-1-cyclohexyl-3-methyl-pyrrolidin-2-one in methanol, add ammonium chloride (11.7 mg, 0.22 mmol) and evaporate methanol out of the mixture three times to give the desired title compound (94 mg, 27%). MS (ES+) m/z=383.

Workup

  1. customevaporate methanol out of the mixture three times

Sources & evidence

ORD record
ord-7e829e2864534dc7ae972df7ee7d0df2
Source dataset
uspto-grants-2010_05
Patent number
US07713979B2

Reaction notes

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