Triethylamine → 3-(4-Methoxy-phenyl)-N-propyl-propionamide

HRID 968860Notes

Reaction equation

HRID 968860 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][C:11]([OH:13])=O)=[CH:5][CH:4]=1.Cl.[CH2:15]([NH2:18])[CH2:16][CH3:17].C(N(CC)CC)C>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:9][CH2:10][C:11]([NH:18][CH2:15][CH2:16][CH3:17])=[O:13])=[CH:7][CH:8]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 11165Propylamine hydrochlorideHCID 957503-(p-Methoxyphenyl)propionic acid

Product 1

HCID 51850723-(4-Methoxy-phenyl)-N-propyl-propionamide

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 3-(4-methoxyphenyl)propionic acid (8.0 g, 44.4 mmol), propylamine hydrochloride (4.24 g, 44.4 mmol), 4-dimethylaminopyridine (0.65 g, 5.33 mmol) and triethylamine (6.9 mL, 48.96 mmol) in methylene chloride (70 mL) was added 1-[(3-dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (10.21 g, 53.28 mmol). The reaction mixture was stirred overnight at ambient temperature followed by dilution with methylene chloride. The mixture was washed with 1N hydrochloric acid, 2N sodium hydroxide, water, brine and dried. Evaporation of the solvent yielded the pure product (10.36 g; 95.4%): 1HNMR (400 MHz, CDCl3) δ 7.76 (brs, 1H), 7.10 (d, 2H, J=8.8 Hz), 6.79 (d, 2H, J=8.0 Hz), 3.68 (s, 3H), 2.95 (q, 2H, J=5.6 Hz). 2.71 (t, 2H, J=7.6 Hz), 2.28 (t, 2H, J=7.2 Hz), 1.34 (m, 2H), 0.77 (t, 3H, J=7.2 Hz); ESMS m/z (relative intensity) 222.2 (M+H+, 100).

Workup

  1. washThe mixture was washed with 1N hydrochloric acid, 2N sodium hydroxide, water, brine
  2. customdried
  3. customEvaporation of the solvent
  4. customyielded the pure product (10.36 g; 95.4%)

Sources & evidence

ORD record
ord-6b5ac310a7034cf590817e82e429ddbf
Source dataset
uspto-grants-2007_12
Patent number
US07304062B2

Reaction notes

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