O-Methyltyramine → N-(2-p-methoxyphenylethyl)-p-fluorophenylpropionamide

HRID 1071985

Reaction equation

HRID 1071985 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:6]([CH2:7][CH2:8][NH2:9])=[CH:5][CH:4]=1.[F:12][C:13]1[CH:18]=[CH:17][C:16]([CH:19]([CH3:23])[C:20](O)=[O:21])=[CH:15][CH:14]=1.Cl.CN(C)CCCN=C=NCC>ClCCl>[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:6]([CH2:7][CH2:8][NH:9][C:20](=[O:21])[CH:19]([C:16]2[CH:17]=[CH:18][C:13]([F:12])=[CH:14][CH:15]=2)[CH3:23])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 4657O-MethyltyramineHCID 27239152-(4-Fluorophenyl)propionic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 86595127N-(2-p-methoxyphenylethyl)-p-fluorophenylpropionamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred mixture of p-methoxyphenethyl amine (3.28 g, 21.7 mmol), p-fluorophenyl propionic acid (3.31 g, 19.7 mmol), and 150 ml anhydrous dichloromethane was added 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (4.16 g, 21.7 mmol). The mixture was stirred at ambient temperature for 40 hours and then washed with 1N sodium hydroxide, 1N hydrochloric acid, and saturated sodium chloride, dried, filtered and evaporated to a green solid (5.41 g, 91%). 1H NMR (CDCl3) δ 7.18 (m, 2H); 6.98 (m, 4 H); 6.81 (d, 2 H); 5.32 (br s, 1 H); 3.79 (s, 3 H); 3.44 (q, 2 H); 2.90 (t, 2 H); 2.68 (t, 2 H); 2.39 (t, 2 H).

Workup

  1. washwashed with 1N sodium hydroxide, 1N hydrochloric acid, and saturated sodium chloride
  2. customdried
  3. filtrationfiltered
  4. customevaporated to a green solid (5.41 g, 91%)

Sources & evidence

ORD record
ord-82a3d6481c9940d29cbe58b48fd548d2
Source dataset
uspto-grants-2005_06
Patent number
US06908931B2

Linked notes

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