Hydrochloric Acid → 1-[2-[3-(3,4-Dichloro-phenyl)-1-(3,4,5-trimethoxy-benzoyl)-pyrrolidin-3-yl]-ethyl]-4-phenyl-piperidine-4-carboxylic acid

HRID 1682985Notes

Reaction equation

HRID 1682985 reaction equation
C[O:2][C:3]([C:5]1([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[CH2:10][CH2:9][N:8]([CH2:11][CH2:12][C:13]2([C:32]3[CH:37]=[CH:36][C:35]([Cl:38])=[C:34]([Cl:39])[CH:33]=3)[CH2:17][CH2:16][N:15]([C:18](=[O:31])[C:19]3[CH:24]=[C:23]([O:25][CH3:26])[C:22]([O:27][CH3:28])=[C:21]([O:29][CH3:30])[CH:20]=3)[CH2:14]2)[CH2:7][CH2:6]1)=[O:4].[OH-].[Na+].Cl>C(O)C>[Cl:39][C:34]1[CH:33]=[C:32]([C:13]2([CH2:12][CH2:11][N:8]3[CH2:9][CH2:10][C:5]([C:40]4[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=4)([C:3]([OH:4])=[O:2])[CH2:6][CH2:7]3)[CH2:17][CH2:16][N:15]([C:18](=[O:31])[C:19]3[CH:24]=[C:23]([O:25][CH3:26])[C:22]([O:27][CH3:28])=[C:21]([O:29][CH3:30])[CH:20]=3)[CH2:14]2)[CH:37]=[CH:36][C:35]=1[Cl:38]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 541795361-[2-[3-(3,4-Dichloro-phenyl)-1-(3,4,5-trimethoxy-benzoyl)-pyrrolidin-3-yl]-ethyl]-4-phenyl-piperidine-4-carboxylic acid methyl-ester

Product 1

HCID 218311351-[2-[3-(3,4-Dichloro-phenyl)-1-(3,4,5-trimethoxy-benzoyl)-pyrrolidin-3-yl]-ethyl]-4-phenyl-piperidine-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-[2-[3-(3,4-Dichloro-phenyl)-1-(3,4,5-trimethoxybenzoyl)-pyrrolidin-3-yl]-ethyl]-4-phenyl-piperidine-4-carboxylic acid methyl-ester (0.393 g, 0.60 mmol) and NaOH (6 mL, 1N, 6 mmol) were combined in ethanol (12 mL). The mixture was stirred for 48 h at ambient temperature. 1N HCl was added to adjust the pH to 1. The aqueous phase was extracted with ethyl acetate. The organic phase was dried over MgSO4, filtered, and concentrated in vacuo to obtain a residue. The residue was chromatographed on silica gel eluting sequentially with 10% methanol in dichloromethane and then 20% methanol in dichloromethane. The fractions which contained the title compound were washed with H2O, dried over MgSO4, filtered, and concentrated in vacuo to give the title compound:

Workup

  1. extractionThe aqueous phase was extracted with ethyl acetate
  2. dry with materialThe organic phase was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customto obtain a residue
  6. customThe residue was chromatographed on silica gel eluting sequentially with 10% methanol in dichloromethane
  7. washwere washed with H2O
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5c6da490948d44628744b7de8803de4b
Source dataset
uspto-grants-1997_06
Patent number
US05635510

Reaction notes

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