Phenacyl bromide → HCID 131722009, compound

HRID 1954429Notes

Reaction equation

HRID 1954429 reaction equation
[CH2:1]1[C:10]2[C:5](=[CH:6][C:7]([NH:11][C:12]([C:14]3[C:15]([C:20]4[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][CH:21]=4)=[CH:16][CH:17]=[CH:18][CH:19]=3)=[O:13])=[CH:8][CH:9]=2)[CH2:4][CH2:3][NH:2]1.Br[CH2:31][C:32]([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)=O.C(=O)([O-])[O-:41].[K+].[K+]>C(#N)C>[O:41]=[C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:34]1[CH2:32][CH2:31][N:2]1[CH2:3][CH2:4][C:5]2[C:10](=[CH:9][CH:8]=[C:7]([NH:11][C:12]([C:14]3[C:15]([C:20]4[CH:25]=[CH:24][C:23]([C:26]([F:27])([F:28])[F:29])=[CH:22][CH:21]=4)=[CH:16][CH:17]=[CH:18][CH:19]=3)=[O:13])[CH:6]=2)[CH2:1]1

Participants

5

Reactant 3

HCID 6259Phenacyl bromideHCID 11430Potassium CarbonateHCID 110147584'-Trifluoromethyl-biphenyl-2-carboxylic acid (1,2,3,4tetrahydroisoquinolin-6-yl)-amide

Product 1

HCID 131722009HCID 131722009, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Compound (II) (0.30 gm, 0.76 mmole), 2-bromoacetophenone (0.15 g, 0.76 mmole) and potassium carbonate (0.12 gm, 0.83 mmole) were combined in 20 mL of acetonitrile and heated to reflux for 1 hr., and then the solvent was evaporated under vacuum. The residue was dissolved in chloroform and washed with saturated sodium bicarbonate. Purification of the dried organic layer was accomplished with silica gel chromatography using 50% ethyl acetate in hexane as the eluent.

Workup

  1. temperatureheated
  2. temperatureto reflux for 1 hr
  3. custom, and then the solvent was evaporated under vacuum
  4. dissolutionThe residue was dissolved in chloroform
  5. washwashed with saturated sodium bicarbonate
  6. customPurification of the dried organic layer

Sources & evidence

ORD record
ord-6eb7d6bc6b894be9a7d830064d0a8b0b
Source dataset
uspto-grants-2000_09
Patent number
US06121283

Reaction notes

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