Phenacyl bromide → HCID 14368657, compound

HRID 2253715Notes

Reaction equation

HRID 2253715 reaction equation
[CH2:1](Br)[C:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[O:3].[NH2:11][CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=2)=[CH:16][CH:15]=1.C(N(CC)C(C)C)(C)C.[BH4-].[Na+]>C(Cl)Cl.CO>[OH:3][CH:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH2:1][NH:11][CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=2)=[CH:16][CH:15]=1

Participants

7

Reactant 4

HCID 6259Phenacyl bromideHCID 81531DiisopropylethylamineHCID 4311764Sodium borohydrideHCID 14850210HCID 14850210, compound

Product 1

HCID 14368657HCID 14368657, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×

Procedure

4 g (20 mmol) of phenacylbromide are dissolved in 20 ml of methylene chloride and added dropwise to a solution of 4.6 g (20 mmol) of 4'-(2-aminoethyl)-4-methoxy-biphenyl and 3.45 ml (20 mmol) of N,N-diisopropyl-ethylamine and 100 ml of methylene chloride at ambient temperature. After 2 hours, 50 ml of methanol are added and, with slight cooling, 1 g (27 mmol) of sodium borohydride is added in batches. After stirring overnight the mixture is evaporated in vacuo, acidified with dilute hydrochloric acid and stirred for 30 minutes. It is then made alkaline with sodium hydroxide solution and extracted with chloroform. The chloroform evaporation residue is purified by column chromatography on silica gel (eluant: chloroform/methanol=10:1). Finally, it is recrystallised from acetonitrile.

Workup

  1. additionis added in batches
  2. customis evaporated in vacuo
  3. stirringstirred for 30 minutes
  4. extractionextracted with chloroform
  5. customThe chloroform evaporation residue
  6. customis purified by column chromatography on silica gel (eluant: chloroform/methanol=10:1)
  7. customFinally, it is recrystallised from acetonitrile

Sources & evidence

ORD record
ord-495e7dcbd2ec40199e09682d06550e8d
Source dataset
uspto-grants-1993_08
Patent number
US05232946

Reaction notes

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