Dimethylformamide → [3-[[[1-(6-Chlorobenzothiazole-2-yl)piperidine-4-yl]isopropylamino]methyl]phenyl]acetic acid methyl ester

HRID 420593Notes

Reaction equation

HRID 420593 reaction equation
[Cl:1][C:2]1[CH:20]=[CH:19][C:5]2[N:6]=[C:7]([N:9]3[CH2:14][CH2:13][CH:12]([NH:15][CH:16]([CH3:18])[CH3:17])[CH2:11][CH2:10]3)[S:8][C:4]=2[CH:3]=1.[CH3:21][O:22][C:23](=[O:33])[CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([CH2:31]Br)[CH:26]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[CH3:21][O:22][C:23](=[O:33])[CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([CH2:31][N:15]([CH:12]2[CH2:11][CH2:10][N:9]([C:7]3[S:8][C:4]4[CH:3]=[C:2]([Cl:1])[CH:20]=[CH:19][C:5]=4[N:6]=3)[CH2:14][CH2:13]2)[CH:16]([CH3:18])[CH3:17])[CH:26]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 10014651(3-Bromomethyl-phenyl)-acetic acid methyl esterHCID 57966227HCID 57966227, compound

Product 1

HCID 57966261[3-[[[1-(6-Chlorobenzothiazole-2-yl)piperidine-4-yl]isopropylamino]methyl]phenyl]acetic acid methyl esterYield 37.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of [1-(6-chlorobenzothiazole-2-yl)piperidine-4-yl]isopropylamine (159 mg), (3-bromomethylphenyl)acetic acid methyl ester (138 mg), potassium carbonate (107 mg) and dimethylformamide (2 mL) was stirred at 80° C. for 8 hours. To the reaction solution was added water 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 (90 mg). Yield: 37%.

Workup

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

Sources & evidence

ORD record
ord-01c0932a77704c018ac6565d88b64913
Source dataset
uspto-grants-2012_01
Patent number
US08097610B2

Reaction notes

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