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

HRID 2424844Notes

Reaction equation

HRID 2424844 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 result in 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 result in oil
  5. customwas purified by column chromatography with silica gel and methylene chloride/methanol (from 99:1 to 95:5) as eluent

Sources & evidence

ORD record
ord-354337a261d247f8b8bd4e954c2835d0
Source dataset
uspto-grants-2011_06
Patent number
US07964615B2

Reaction notes

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