Phenethylamine → N-(2-phenylethyl)but-3-en-1-amine

HRID 29055

Reaction equation

HRID 29055 reaction equation
[C:1]1([CH2:7][CH2:8][NH2:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:17][CH2:18][CH:19]=[CH2:20]>>[CH2:20]([NH:9][CH2:8][CH2:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[CH2:19][CH:18]=[CH2:17]

Participants

4

Reactant 3

HCID 1001PhenethylamineHCID 11430Potassium CarbonateHCID 21241Homoallyl bromide

Product 1

HCID 16720109N-(2-phenylethyl)but-3-en-1-amineYield 62%

Procedure

To a solution of 2-phenylethylamine (72 mL, 570 mmol) is added K2CO3 (82 g, 570 mmol) and 4-bromo-1-butene (25 g, 185 mmol). The solution is stirred overnight at room temperature. The solution is evaporated to dryness and H2O/EtOAc (1:1) (600 mL) is added. The mixture is extracted with EtOAc (4×150 mL). The organic extracts are combined, dried and concentrated under vacuum. The residue is purified by flash chromatography (silica gel; Hexane/EtOAc 1:8) to provide 20 g (62%) of the title compound. M+H+=176.10.

Workup

  1. customThe solution is evaporated to dryness and H2O/EtOAc (1:1) (600 mL)
  2. additionis added
  3. extractionThe mixture is extracted with EtOAc (4×150 mL)
  4. customdried
  5. concentrationconcentrated under vacuum
  6. customThe residue is purified by flash chromatography (silica gel; Hexane/EtOAc 1:8)

Sources & evidence

ORD record
ord-65898676a2d449a5a2b0568fca6d3bd3
Source dataset
uspto-grants-2008_09
Patent number
US07419975B2

Linked notes

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