Water → HCID 23138736, compound

HRID 1171638Notes

Reaction equation

HRID 1171638 reaction equation
C(O)(=O)C.[O:5]1[CH:9]=[CH:8][CH:7]=[C:6]1/[CH:10]=[C:11]1\[CH2:12][NH:13][CH2:14][CH2:15][CH:16]\1[OH:17].Br[CH:19]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[F:31])[C:20]([CH:22]1[CH2:24][CH2:23]1)=[O:21].C(N(CC)CC)C.O>CN(C)C=O>[CH:22]1([C:20](=[O:21])[CH:19]([N:13]2[CH2:14][CH2:15][CH:16]([OH:17])/[C:11](=[CH:10]/[C:6]3[O:5][CH:9]=[CH:8][CH:7]=3)/[CH2:12]2)[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[F:31])[CH2:24][CH2:23]1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 23138601HCID 23138601, compoundHCID 234358712-Bromo-1-cyclopropyl-2-(2-fluorophenyl)ethan-1-one

Product 1

HCID 23138736HCID 23138736, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (E)-3-[(furan-2-yl)methylidene]piperidin-4-ol hydrogen acetate (2.81 g) and 2-bromo-2-(2-fluorophenyl)-1-cyclopropylethanone (2.71 g) in N,N-dimethylformamide (60 ml) was added triethylamine (1.22 ml) under ice-cooling, and the resulting mixture was stirred at room temperature for 1 hour. After stirring, water was added to the reaction mixture, and the resulting mixture was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium chloride solution, and the organic layer was dried over anhydrous sodium sulfate. The solvent was removed in vacuo, and the residue was purified by chromatography on a silica gel column using a mixed solvent of ethyl acetate and hexane (3:7 to 1:1) as the eluent to afford the title compound (2.30 g, yield: 74%) as a pale yellow amorphous solid.

Workup

  1. temperaturecooling
  2. stirringAfter stirring
  3. extractionthe resulting mixture was extracted with ethyl acetate
  4. washThe extract was washed with saturated aqueous sodium chloride solution
  5. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  6. customThe solvent was removed in vacuo
  7. customthe residue was purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-513c5f0d90674fbfb122305500ed2a22
Source dataset
uspto-grants-2010_11
Patent number
US07829580B2

Reaction notes

Loading…