Acetic Acid → HCID 57966227, compound

HRID 420592Notes

Reaction equation

HRID 420592 reaction equation
[Cl:1][C:2]1[CH:17]=[CH:16][C:5]2[N:6]=[C:7]([N:9]3[CH2:14][CH2:13][CH:12]([NH2:15])[CH2:11][CH2:10]3)[S:8][C:4]=2[CH:3]=1.[CH3:18][C:19]([CH3:21])=O.C(O)(=O)C>CO>[Cl:1][C:2]1[CH:17]=[CH:16][C:5]2[N:6]=[C:7]([N:9]3[CH2:10][CH2:11][CH:12]([NH:15][CH:19]([CH3:21])[CH3:18])[CH2:13][CH2:14]3)[S:8][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 180AcetoneHCID 57966284HCID 57966284, compound

Product 1

HCID 57966227HCID 57966227, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 1-(6-chlorobenzothiazole-2-yl)piperidine-4-ylamine (335 mg), acetone (92 ul), acetic acid (0.1 mL) and methanol (3 mL) was stirred at room temperature for 5 minutes. To the reaction solution was added triacetoxy sodium boron hydride (332 mg). The mixture was stirred at room temperature for 16 hours. The reaction solution was concentrated under reduced pressure. Aqueous sodium hydrogencarbonate was added thereto 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 residue was purified by column chromatograph on silica gel to give the title compound (160 mg). Yield: 41%.

Workup

  1. stirringThe mixture was stirred at room temperature for 16 hours
  2. concentrationThe reaction solution was concentrated under reduced pressure
  3. additionAqueous sodium hydrogencarbonate was added
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with water and brine
  6. dry with materialdried over sodium sulphate
  7. customThe solvent was evaporated under reduced pressure
  8. customthe residue was purified by column chromatograph on silica gel

Sources & evidence

ORD record
ord-f4a44c94952246b4ac893645ba4a7493
Source dataset
uspto-grants-2012_01
Patent number
US08097610B2

Reaction notes

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