Hydrochloric Acid → HCID 66658364, compound

HRID 420591Notes

Reaction equation

HRID 420591 reaction equation
C[O:2][C:3](=[O:31])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH2:11][NH:12][CH2:13][CH2:14][CH:15]2[CH2:20][CH2:19][N:18]([C:21]3[S:22][C:23]4[CH:29]=[C:28]([Cl:30])[CH:27]=[CH:26][C:24]=4[N:25]=3)[CH2:17][CH2:16]2)[CH:6]=1.[OH-].[Na+].O1CCCC1.Cl>CO>[Cl:30][C:28]1[CH:27]=[CH:26][C:24]2[N:25]=[C:21]([N:18]3[CH2:19][CH2:20][CH:15]([CH2:14][CH2:13][NH:12][CH2:11][C:7]4[CH:6]=[C:5]([CH2:4][C:3]([OH:31])=[O:2])[CH:10]=[CH:9][CH:8]=4)[CH2:16][CH2:17]3)[S:22][C:23]=2[CH:29]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 66658025HCID 66658025, compound

Product 1

HCID 66658364HCID 66658364, compoundYield 30.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of [3-[[[1-(6-chlorobenzothiazole-2-yl)piperidine-4-yl]ethylamino]methyl]phenyl]acetic acid methyl ester (65 mg), 2N sodium hydroxide (0.36 mL), tetrahydrofuran (1 mL) and methanol (1 mL) was stirred at room temperature for 1 hour. The solution was neutralized with 2N hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with water and brine, and dried over sodium sulphate. The solvent was evaporated under reduced pressure and the obtained residue was washed with the mixed solvent of ethyl acetate and n-hexane to give the title compound (19 mg). Yield: 30%.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over sodium sulphate
  4. customThe solvent was evaporated under reduced pressure
  5. washthe obtained residue was washed with the mixed solvent of ethyl acetate and n-hexane

Sources & evidence

ORD record
ord-583be9a49610475087804f2b999cc63f
Source dataset
uspto-grants-2012_01
Patent number
US08097610B2

Reaction notes

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