Hydrochloric Acid → HCID 57966369, compound

HRID 420594Notes

Reaction equation

HRID 420594 reaction equation
C[O:2][C:3](=[O:32])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH2:11][N:12]([CH:16]2[CH2:21][CH2:20][N:19]([C:22]3[S:23][C:24]4[CH:30]=[C:29]([Cl:31])[CH:28]=[CH:27][C:25]=4[N:26]=3)[CH2:18][CH2:17]2)[CH:13]([CH3:15])[CH3:14])[CH:6]=1.[OH-].[Na+].O1CCCC1.Cl>CO>[Cl:31][C:29]1[CH:28]=[CH:27][C:25]2[N:26]=[C:22]([N:19]3[CH2:20][CH2:21][CH:16]([N:12]([CH2:11][C:7]4[CH:6]=[C:5]([CH2:4][C:3]([OH:32])=[O:2])[CH:10]=[CH:9][CH:8]=4)[CH:13]([CH3:14])[CH3:15])[CH2:17][CH2:18]3)[S:23][C:24]=2[CH:30]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 57966261[3-[[[1-(6-Chlorobenzothiazole-2-yl)piperidine-4-yl]isopropylamino]methyl]phenyl]acetic acid methyl ester

Product 1

HCID 57966369HCID 57966369, compoundYield 32.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of [3-[[[1-(6-chlorobenzothiazole-2-yl)piperidine-4-yl]isopropylamino]methyl]phenyl]acetic acid methyl ester (90 mg), 2N sodium hydroxide (0.5 mL), tetrahydrofuran (2 mL) and methanol (1 mL) was stirred at room temperature for 1 hour. After neutralizing with 2N hydrochloric acid, the reaction solution was concentrated under reduced pressure and extracted with ethyl acetate. The organic layer was washed with water and brine, and dried over magnesium sulphate. The solvent was evaporated under reduced pressure and the residue was purified by column chromatograph on silica gel to give the title compound (28 mg).

Workup

  1. concentrationthe reaction solution was concentrated under reduced pressure
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over magnesium sulphate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by column chromatograph on silica gel

Sources & evidence

ORD record
ord-b45cd8bcd805431db5daee26ea3d4e92
Source dataset
uspto-grants-2012_01
Patent number
US08097610B2

Reaction notes

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