Benzylamine → N-benzyl-6-(2,2-difluoro-2-phenylethoxy)hexan-1-amine

HRID 885545Notes

Reaction equation

HRID 885545 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][CH2:9][C:10]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)([F:12])[F:11].[CH2:19]([NH2:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C(OCC)C>[CH2:19]([NH:26][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][CH2:9][C:10]([F:12])([F:11])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

4

Reactant 2

HCID 7504BenzylamineHCID 67245921(2-((6-Bromohexyl)oxy)-1,1-difluoroethyl)benzene

Product 1

HCID 67245081N-benzyl-6-(2,2-difluoro-2-phenylethoxy)hexan-1-amineYield 59%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of Intermediate 7 (5.0 g, 15.6 mmol) and benzyl amine (3.4 mL, 31.1 mmol) was heated at 120° C. for two hours. The crude reaction was treated with ethyl ether and the resulting solid was filtered. The solvent was concentrated and the resulting oil was purified by column chromatography with silica gel and methylene chloride/methanol (from 99:1 to 95:5) as eluent, to yield N-benzyl-6-(2,2-difluoro-2-phenylethoxy)hexan-1-amine (3.2 g, 59%) as oil.

Workup

  1. customThe crude reaction
  2. filtrationthe resulting solid was filtered
  3. concentrationThe solvent was concentrated
  4. customthe resulting oil was purified by column chromatography with silica gel and methylene chloride/methanol (from 99:1 to 95:5) as eluent

Sources & evidence

ORD record
ord-2ce3accf72434c2fb5eb6ed30a4b86e5
Source dataset
uspto-grants-2012_08
Patent number
US08242177B2

Reaction notes

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