Water → Oxalate

HRID 2404460Notes

Reaction equation

HRID 2404460 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH:10]([O:27][CH:28]1[CH2:33][CH2:32][N:31]([CH3:34])[CH2:30][CH2:29]1)[C:11]1[CH:12]=[C:13]([N:17]2[CH2:22][CH2:21][CH:20]([O:23][C:24](=[O:26])[CH3:25])[CH2:19][CH2:18]2)[CH:14]=[CH:15][CH:16]=1.[OH-:35].[Na+].[OH2:37]>CO>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH:10]([O:27][CH:28]1[CH2:33][CH2:32][N:31]([CH3:34])[CH2:30][CH2:29]1)[C:11]1[CH:12]=[C:13]([N:17]2[CH2:22][CH2:21][CH:20]([OH:23])[CH2:19][CH2:18]2)[CH:14]=[CH:15][CH:16]=1.[C:25]([O-:37])(=[O:35])[C:24]([O-:23])=[O:26]

Participants

6

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 66836026HCID 66836026, compound

Product 2

HCID 71081OxalateHCID 66836101HCID 66836101, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of acetic acid 1-{3-[benzothiazol-2-yl(1-methylpiperidin-4-yloxy)methyl]phenyl}piperidin-4-yl ester (example 413, 100 mg) and aqueous 1N sodium hydroxide in methanol (1 mL) is stirred at room temperature for 30 min. The mixture is diluted water and extracted with dichloromethane. The pooled organic extracts are dried over magnesium sulfate and concentrated under reduced pressure. The residue is purified by chromatography (gradient dichloromethane/methanol/ammonia from 95/5/0.5 to 90/10/0.5). The base is converted into its oxalate salt in acetone to give 1-{3-[benzothiazol-2-yl(1-methylpiperidin-4-yloxy)methyl]phenyl}piperidin-4-ol, oxalate melting at 110° C.

Workup

  1. extractionextracted with dichloromethane
  2. dry with materialThe pooled organic extracts are dried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue is purified by chromatography (gradient dichloromethane/methanol/ammonia from 95/5/0.5 to 90/10/0.5)

Sources & evidence

ORD record
ord-aff23fb6d5fa44d184c3a28101f7f84e
Source dataset
uspto-grants-2014_08
Patent number
US08802664B2

Reaction notes

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