HCID 87770298, compound → HCID 23146388, compound

HRID 2378000Notes

Reaction equation

HRID 2378000 reaction equation
Br[C:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][C:3]=1[CH2:11][CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][N:13]1[C:18](=[O:23])[C:19]([F:22])([F:21])[F:20].[Cu][C:25]#[N:26]>CN1CCCC1=O.O.N.C(OCC)(=O)C>[F:20][C:19]([F:22])([F:21])[C:18]([N:13]1[CH2:14][CH2:15][CH2:16][CH2:17][CH:12]1[CH2:11][C:3]1[O:4][C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[C:2]=1[C:25]#[N:26])=[O:23]

Participants

7

Reactant 2

HCID 87770298HCID 87770298, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 23146388HCID 23146388, compound

Reagents, catalysts & solvents 4

HCID 222AmmoniaSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To a solution of (RS)-1-(2-3-bromo-benzofuran-2-ylmethyl-piperidin-1-yl)-2,2,2-trifluoro-ethanone, D41 (840 mg, 2.1 mmol) in N-methylpyrrolidinone (15 ml) was added copper(I)cyanide (387 mg, 4.2 mmol) and the mixture refluxed for 4.5 h. The reaction mixture was cooled sand diluted with water (100 ml), 0.880 ammonia (3 ml) and ethyl acetate (3×). The combined extracts were dried (Na2SO4) and the solvent removed in vacuo. The residual oil was redissolved in ethyl acetate (75 ml) and washed with water (4×), brine, dried (Na2SO4) and the solvent removed in vacuo. Chromatography (silica gel) afforded the title compound as a solid.

Workup

  1. temperaturethe mixture refluxed for 4.5 h
  2. temperatureThe reaction mixture was cooled sand
  3. dry with materialThe combined extracts were dried (Na2SO4)
  4. customthe solvent removed in vacuo
  5. dissolutionThe residual oil was redissolved in ethyl acetate (75 ml)
  6. washwashed with water (4×), brine
  7. dry with materialdried (Na2SO4)
  8. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-f7bbc421eab44d1aa48e65f9e825dd0b
Source dataset
uspto-grants-2008_12
Patent number
US07470710B2

Reaction notes

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