Sodium Hydroxide → HCID 57964332, compound

HRID 2403531Notes

Reaction equation

HRID 2403531 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][N:16]2[CH2:21][CH2:20][N:19]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([O:30]CC)=[O:29])[CH:23]=3)[CH2:18][CH2:17]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([CH2:14][CH2:15][N:16]2[CH2:17][CH2:18][N:19]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([OH:30])=[O:29])[CH:23]=3)[CH2:20][CH2:21]2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 69070952HCID 69070952, compound

Product 1

HCID 57964332HCID 57964332, compoundYield 47%

Procedure

To a solution of 2.8 g (12.8 mmol) of 4-{2-[4-(3-ethoxycarbonylphenyl)piperazin-1-yl]ethyl}piperidine-1-carboxylic acid tert-butyl ester are added 12.8 mL of 1N aqueous sodium hydroxide solution. The mixture is stirred overnight at room temperature then concentrated under reduced pressure. The residue is acidified with 12.8 mL of 1N aqueous hydrochloric acid solution. The product is extracted with ethyl acetate, washed with water, dried over magnesium sulfate, filtered and concentrated under reduced pressure to give 2.5 g (47%) of 4-{2-[4-(3-carboxyphenyl)piperazin-1-yl]ethyl}piperidine-1-carboxylic acid tert-butyl ester.

Workup

  1. concentrationthen concentrated under reduced pressure
  2. extractionThe product is extracted with ethyl acetate
  3. washwashed with water
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-92288823a5a84c7ab03dc036ff821675
Source dataset
uspto-grants-2014_08
Patent number
US08802678B2

Reaction notes

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