Potassium Carbonate → HCID 69929639, compound

HRID 2186798Notes

Reaction equation

HRID 2186798 reaction equation
Cl.[F:2][C:3]1[CH:4]=[CH:5][C:6]2[C:10]([CH:11]3[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][CH2:19][C:20]([C:22]4[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=4)=[O:21])[CH2:13][CH2:12]3)=[CH:9][S:8][C:7]=2[CH:29]=1.C(=O)([O-])[O-].[K+].[K+].CO[CH:38](OC)[N:39]([CH3:41])[CH3:40].N1CC[CH2:46][CH2:45]1>CN(C)C=O>[F:2][C:3]1[CH:4]=[CH:5][C:6]2[C:10]([CH:11]3[CH2:12][CH2:13][N:14]([CH2:17][CH2:18][C:19](=[CH:41][N:39]4[CH2:38][CH2:46][CH2:45][CH2:40]4)[C:20]([C:22]4[CH:23]=[CH:24][C:25]([F:28])=[CH:26][CH:27]=4)=[O:21])[CH2:15][CH2:16]3)=[CH:9][S:8][C:7]=2[CH:29]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 31268PyrrolidineHCID 78373Dimethylformamide dimethyl acetalHCID 22649335HCID 22649335, compound

Product 1

HCID 69929639HCID 69929639, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 0.15 g of 6-fluoro-3-[1-[4-(4-fluorophenyl)-4-oxobutyl]piperidin-4-yl]benzo[b]thiophene hydrochloride, 0.05 g of anhydrous potassium carbonate, 0.36 ml of N,N-dimethylformamide dimethyl acetal, 0.25 ml of pyrrolidine and 0.5 ml of N,N-dimethylformamide was stirred on an oil bath at 120° C. for 3.5 hours. The reaction mixture was cooled to room temperature and then separated with ethyl acetate and water, and the aqueous layer was extracted with ethyl acetate. The combined organic layer was washed three times with a saturated aqueous sodium chloride solution. After drying over magnesium sulfate, the solvent was distilled off under reduced pressure to obtain crude 6-fluoro-3-[1-[3-(1-pyrrolidinomethylene)-4-(4-fluorophenyl)-4-oxobutyl]piperidin-4-yl]benzo[b]thiophene.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customseparated with ethyl acetate and water
  3. extractionthe aqueous layer was extracted with ethyl acetate
  4. washThe combined organic layer was washed three times with a saturated aqueous sodium chloride solution
  5. dry with materialAfter drying over magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-bf7d59f297c44f5f9dbba222c39be2f1
Source dataset
uspto-grants-2002_06
Patent number
US06407121B1

Reaction notes

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