Ethyl Bromide → HCID 57849555, compound

HRID 737113Notes

Reaction equation

HRID 737113 reaction equation
[C:1]1([CH:7]2[NH:12][CH2:11][CH2:10][N:9]([CH2:13][C:14]3[CH:19]=[CH:18][C:17]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=4[C:26]([F:29])([F:28])[F:27])=[CH:16][CH:15]=3)[CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:30](N(CC)C(C)C)(C)[CH3:31].BrCC>C1COCC1.ClCCl>[CH2:30]([N:12]1[CH2:11][CH2:10][N:9]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[C:26]([F:28])([F:29])[F:27])=[CH:16][CH:15]=2)[CH2:8][CH:7]1[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[CH3:31]

Participants

6

Reactant 3

HCID 6332Ethyl BromideHCID 81531DiisopropylethylamineHCID 57849459HCID 57849459, compound

Product 1

HCID 57849555HCID 57849555, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

100 mg of 3-phenyl-1-(2′-trifluoromethyl-biphenyl-4-ylmethyl)-piperazine were dissolved in THF, 2 equiv. of N,N-diisopropylethylamine were added followed by 2 equiv. of bromoethane. The reaction was stirred at 80° C. overnight. The reaction was diluted with dichloromethane and washed with 1N aqueous NaOH solution. The organic layers were dried over Na2SO4, filtered and concentrated in vacuo. The crude residue was purified by column chromatography to afford 1-ethyl-2-phenyl-4-(2′-trifluoromethyl-biphenyl-4-ylmethyl)-piperazine as the free base. Addition of 1 equiv. of 1M HCl in dioxane and drying in vacuo afforded the title compound as hydrochloride salt. Yield 35% ES MS m/z 425

Workup

  1. washwashed with 1N aqueous NaOH solution
  2. dry with materialThe organic layers were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude residue was purified by column chromatography

Sources & evidence

ORD record
ord-8b5002b363c64cb18a56c0d02ac07e25
Source dataset
uspto-grants-2009_09
Patent number
US07595397B2

Reaction notes

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