Water → Oxalate

HRID 572870Notes

Reaction equation

HRID 572870 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-df262763719d426ba072bc06fc541e0f
Source dataset
uspto-grants-2015_05
Patent number
US09029357B2

Reaction notes

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