1,3-Dibromopropane → (3-Bromo-propyl)-(2-chloro-3-trifluoromethyl-benzyl)diphenylethyl-amine

HRID 902760Notes

Reaction equation

HRID 902760 reaction equation
[Cl:1][C:2]1[C:23]([C:24]([F:27])([F:26])[F:25])=[CH:22][CH:21]=[CH:20][C:3]=1[CH2:4][NH:5][CH2:6][CH:7]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[Br:28][CH2:29][CH2:30][CH2:31]Br.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Br:28][CH2:29][CH2:30][CH2:31][N:5]([CH2:4][C:3]1[CH:20]=[CH:21][CH:22]=[C:23]([C:24]([F:25])([F:26])[F:27])[C:2]=1[Cl:1])[CH2:6][CH:7]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 80011,3-DibromopropaneHCID 11430Potassium CarbonateHCID 58913799(2-Chloro-3-trifluoromethyl-benzyl)-diphenylethyl-amine

Product 1

HCID 57757127(3-Bromo-propyl)-(2-chloro-3-trifluoromethyl-benzyl)diphenylethyl-amineYield 67%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of compound (2-Chloro-3-trifluoromethyl-benzyl)-diphenylethyl-amine (2.5 g, 6.5 mmol) and 1,3-dibromo propane (3.2 ml, 32 mmol) in acetonitrile (300 ml) was treated with solid potassium carbonate (1.8 g, 13 mmol). The reaction was heated to reflux and stirred for 48 h. Upon cooling to room temperature, the reaction was filtered through a pad of celite, washed with EtOAc, and the filtrate was concentrated in vacuo. The crude product was purified by column chromatography (EtOAc:Hexane/20:80) to give the title compound as an oil (2.2 g, 67%). MS m/e 510.6 (M+H)+.

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux
  3. filtrationthe reaction was filtered through a pad of celite
  4. washwashed with EtOAc
  5. concentrationthe filtrate was concentrated in vacuo
  6. customThe crude product was purified by column chromatography (EtOAc:Hexane/20:80)

Sources & evidence

ORD record
ord-10f31a92ce9b4be793dc55e15a33a8de
Source dataset
uspto-grants-2008_04
Patent number
US07365085B2

Reaction notes

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