Phenethylamine → Methyl 7-[(2-phenylethyl)amino]heptanoate

HRID 1080543Notes

Reaction equation

HRID 1080543 reaction equation
[C:1]1([CH2:7][CH2:8][NH2:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.Br[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]([O:26][CH3:27])=[O:25]>C1(C)C=CC=CC=1>[C:1]1([CH2:7][CH2:8][NH:9][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]([O:26][CH3:27])=[O:25])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 1001PhenethylamineHCID 8471TriethylamineHCID 554086Methyl 7-bromoheptanoate

Product 1

HCID 19047852Methyl 7-[(2-phenylethyl)amino]heptanoateYield 26.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a mixture of 2-phenylethylamine (1.09 g, 9 mmol) and triethylamine (1.37 g, 13.5 mmol) in toluene (50 mL) was added methyl 7-bromoheptanoate (2.0 g, 9 mmol) and refluxed overnight. The reaction mixture was filtered and concentrated. Flash column chromatography over silica gel using 100% ethyl acetate yielded a yellow oil (0.62 g, 20%) NMR (250 MHz, CDCl3), 1.12-1.40 (4H, m), 1.40-1.72 (4H, m), 2.29 (2H, t), 2.63 (2H, t), 2.75-2.96 (4H, m), 2.96-3.1 (1H, br s), 3.66 (3H, s), 7.00-7.38 (5H, m).

Workup

  1. temperaturerefluxed overnight
  2. filtrationThe reaction mixture was filtered
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-e95dfc1554da448ea3cbc270fedb5d36
Source dataset
uspto-grants-1996_12
Patent number
US05580896

Reaction notes

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