Dimethylformamide → n-[5-(2-Acetylaminoethyl)-2-methoxyphenyl]-3-oxo-butyramide

HRID 551601Notes

Reaction equation

HRID 551601 reaction equation
Cl.[NH2:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][NH:13][C:14](=[O:16])[CH3:15])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].CN(C)C=O.[CH2:22]=[C:23]1[O:27][C:25](=[O:26])[CH2:24]1.C(N(CC)CC)C>O>[C:14]([NH:13][CH2:12][CH2:11][C:5]1[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([NH:2][C:25](=[O:26])[CH2:24][C:23](=[O:27])[CH3:22])[CH:4]=1)(=[O:16])[CH3:15]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 12661DiketeneHCID 45074592N-(3-Amino-4-methoxyphenethyl)acetamide hydrochloride

Product 1

HCID 58939150n-[5-(2-Acetylaminoethyl)-2-methoxyphenyl]-3-oxo-butyramideYield 96.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
82.5 °C

Procedure

N-[-2-(3-amino-4-methoxyphenyl)ethyl]acetamide hydrochloride (19 g) was mixed with 40 mL N,N-dimethylformamide and 18 g of diketene followed by slow addition of 3 mL of triethylamine. The mixture was stirred at 80-85° C. for 30 minutes and then poured into 300 mL of water. The aqueous solution was extracted with chloroform (2×200 mL) and the solvent was removed by rotary evaporation to yield 21.9 g (96.5%) of N-[5-(2-acetylaminoethyl)-2-methoxyphenyl]-3-oxo-butyramide as a light yellow oil. 1HNMR (DMSO-d6) spectrum was consistent with the desired product.

Workup

  1. extractionThe aqueous solution was extracted with chloroform (2×200 mL)
  2. customthe solvent was removed by rotary evaporation

Sources & evidence

ORD record
ord-d6c0a23da664424881c8cbc813461061
Source dataset
uspto-grants-2011_05
Patent number
US07947761B2

Reaction notes

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