Sodium Hydroxide → 1-[2-[1-Benzoyl-3-(3,4-dichlorophenyl)-pyrrolidin-3-yl]-ethyl]-4-phenylpiperidine-4-carboxylic acid

HRID 1682947Notes

Reaction equation

HRID 1682947 reaction equation
C[O:2][C:3]([C:5]1([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH2:10][CH2:9][N:8]([CH2:11][CH2:12][C:13]2([C:26]3[CH:31]=[CH:30][C:29]([Cl:32])=[C:28]([Cl:33])[CH:27]=3)[CH2:17][CH2:16][N:15]([C:18](=[O:25])[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:14]2)[CH2:7][CH2:6]1)=[O:4].[OH-].[Na+]>C(O)C>[C:18]([N:15]1[CH2:16][CH2:17][C:13]([CH2:12][CH2:11][N:8]2[CH2:7][CH2:6][C:5]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)([C:3]([OH:4])=[O:2])[CH2:10][CH2:9]2)([C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[C:28]([Cl:33])[CH:27]=2)[CH2:14]1)(=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 539315011-[2-[1-Benzoyl-3-(3,4-dichloro-phenyl)-pyrrolidin-3-yl]-ethyl]-4-phenyl-piperidine-4-carboxylic acid methyl ester

Product 1

HCID 540387971-[2-[1-Benzoyl-3-(3,4-dichlorophenyl)-pyrrolidin-3-yl]-ethyl]-4-phenylpiperidine-4-carboxylic acidYield 43%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-[2-[1-Benzoyl-3-(3,4-dichloro-phenyl)-pyrrolidin-3-yl]-ethyl]-4-phenyl-piperidine-4-carboxylic acid methyl ester (0.2850 g, 0.5 mmol) was dissolved in ethanol (10 mL) and treated with 1M sodium hydroxide (5 mL, 5 mmol) at 20° C. for 2 hours. The aqueous phase was washed with ethyl acetate. The aqueous phase was acidified with 1N hydrochloric acid, and then extracted with ethyl acetate. The organic phase was dried over magnesium sulfate, filtered, and concentrated in vacuo to give 0.117 g (43%) of the title compound.

Workup

  1. washThe aqueous phase was washed with ethyl acetate
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic phase was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7cf13466e10e4e5996373ec9927b1c10
Source dataset
uspto-grants-1997_06
Patent number
US05635510

Reaction notes

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