Methylamine → 2-(4-methoxyphenyl)-N-methylacetamide

HRID 6727

Reaction equation

HRID 6727 reaction equation
Cl.[CH3:2][N:3](C)CCCN=C=NCC.[CH3:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][C:22]([OH:24])=O)=[CH:17][CH:16]=1.O.ON1C2C=CC=CC=2C=NN1.CN>O1CCCC1>[CH3:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][C:22]([NH:3][CH3:2])=[O:24])=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 6329MethylamineHCID 76904-Methoxyphenylacetic AcidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 220185051-Hydroxybenzotriazine hydrate

Product 1

HCID 32645502-(4-methoxyphenyl)-N-methylacetamideYield 83.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Solid 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.60 g) was added to a stirred suspension of (4-methoxyphenyl)acetic acid (0.50 g) and 1-hydroxybenzotriazine hydrate (0.40 g) in 10 mL tetrahydrofuran. The mixture was stirred for 30 min, then methylamine (2.0 M in THF, 6.0 mL) was added. Stirring was continued for 12 h and the volatile material was subsequently evaporated. The crude residue was dissolved in 50 mL of EtOAc and washed twice with 50 mL of 1 M hydrochloric acid, twice with 50 mL of saturated sodium bicarbonate, and twice with 50 mL of saturated sodium chloride. Evaporation of the ethyl acetate gives 0.45 g of 2-(4-methoxyphenyl)-N-methylacetamide.

Workup

  1. stirringStirring
  2. waitwas continued for 12 h
  3. customthe volatile material was subsequently evaporated
  4. dissolutionThe crude residue was dissolved in 50 mL of EtOAc
  5. washwashed twice with 50 mL of 1 M hydrochloric acid, twice with 50 mL of saturated sodium bicarbonate
  6. customEvaporation of the ethyl acetate

Sources & evidence

ORD record
ord-daa6f6f4c0d14c2293be4cc625e0a459
Source dataset
uspto-grants-2006_08
Patent number
US07084154B2

Linked notes

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