Hydrochloric Acid → HCID 68304435, compound

HRID 1846674Notes

Reaction equation

HRID 1846674 reaction equation
C([O:3][C:4](=[O:28])[CH2:5][CH:6]1[CH2:11][CH2:10][N:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[NH:18][C:19](=[O:27])[C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[CH:21]=2)[CH2:8][CH2:7]1)C.CO.[OH-].[Na+].Cl>O>[Cl:26][C:22]1[CH:21]=[C:20]([CH:25]=[CH:24][CH:23]=1)[C:19]([NH:18][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[N:9]1[CH2:10][CH2:11][CH:6]([CH2:5][C:4]([OH:28])=[O:3])[CH2:7][CH2:8]1)=[O:27]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 68304436HCID 68304436, compound

Product 1

HCID 68304435HCID 68304435, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
60 °C

Procedure

To a suspension of 0.34 g (0.85 mmol) of {1-[2-(3-chloro-benzoylamino)-phenyl]-piperidin-4-yl}-acetic acid ethyl ester in a 1:1 mixture of water:methanol (10 mL) is added 0.64 mL (1.6 mmol) of sodium hydroxide as a 10% aqueous solution. The mixture is heated to 60° C. for 3 hours then cooled to room temperature, diluted with water, and the pH of the mixture is adjusted to approximately pH 5 by the addition of a 2 N solution of hydrochloric acid. The mixture is extracted with ethyl acetate and the combined organic phase is dried over anhydrous sodium sulfate and concentrated under reduced pressure to provide 0.29 g (92%) of {1-[2-(3-chloro-benzoylamino)-phenyl]-piperidin-4-yl}-acetic acid as a yellow oil.

Workup

  1. temperaturethen cooled to room temperature
  2. extractionThe mixture is extracted with ethyl acetate
  3. dry with materialthe combined organic phase is dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e50ab42d5b10460982eca43e4cd5d26e
Source dataset
uspto-grants-2015_02
Patent number
US08952004B2

Reaction notes

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