Allylamine → HCID 28563318, compound

HRID 2251545Notes

Reaction equation

HRID 2251545 reaction equation
[CH2:1]([NH2:4])[CH:2]=[CH2:3].[F:5][C:6]([F:17])([F:16])[O:7][C:8]1[CH:15]=[CH:14][C:11]([CH2:12]Br)=[CH:10][CH:9]=1.CCN(C(C)C)C(C)C>ClCCl>[F:5][C:6]([F:17])([F:16])[O:7][C:8]1[CH:15]=[CH:14][C:11]([CH2:12][NH:4][CH2:1][CH:2]=[CH2:3])=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 7853AllylamineHCID 81531DiisopropylethylamineHCID 1427851-(Bromomethyl)-4-(trifluoromethoxy)benzene

Product 1

HCID 28563318HCID 28563318, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of allylamine (17.8 g; 312 mmol) in 200 ml of dichloromethane was added 4-trifluoromethoxybenzyl bromide (16 g; 62.4 mmol) and DIEA 8.88 g; 68.4 mmol). After stirring at rt overnight the reaction mixture was extracted with one volume of water. The organic phase was dried over sodium sulfate and concentrated to afford N-[4-(trifluoromethoxy)benzyl]prop-2-en-1-amine (14 g; 97% crude yield), which was used in the next step without further purification.

Workup

  1. extractionwas extracted with one volume of water
  2. dry with materialThe organic phase was dried over sodium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-e455ea3dd15e40bca18913fee2564c40
Source dataset
uspto-grants-2008_01
Patent number
US07319104B2

Reaction notes

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