Water → HCID 19850164, compound

HRID 542540Notes

Reaction equation

HRID 542540 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH2:10][CH2:11][NH:12][C:13](=[O:18])[C:14]([F:17])([F:16])[F:15])[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].I[CH3:20].O>CN(C)C=O>[F:17][C:14]([F:15])([F:16])[C:13]([NH:12][CH2:11][CH2:10][C:4]1[CH:5]=[CH:6][C:7]([O:8][CH3:9])=[C:2]([NH:1][CH3:20])[CH:3]=1)=[O:18]

Participants

5

Reactant 3

HCID 962WaterHCID 6328Methyl iodideHCID 12807541N-[2-(3-Amino-4-methoxyphenyl)ethyl]-2,2,2-trifluoroacetamide

Product 1

HCID 19850164HCID 19850164, compoundYield 22.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-[2-(3amino-4-methoxyphenyl]ethyl]-2,2,2-trifluoro acetamide (26.2 g., 0.1 mole) and iodomethane (14.0 g., 6.2 ml , 0.1 mole) in dry dimethylformamide (500 ml) were stirred under nitrogen for 3 hr. The solution was poured into water and the suspension extracted with ethyl acetate. Evaporation of the extracts afforded an oil which was separated by high pressure liquid chromatography on silica using 1% methanol in dichloromethane as eluant. Evaporation of the fractions containing the major bond afforded the sub-title compound (6.1 g) as a white solid mp 65°-67°. The hydrochloride, prepared in the usual way, had mp 153°-155°.

Workup

  1. extractionthe suspension extracted with ethyl acetate
  2. customEvaporation of the extracts
  3. customafforded an oil which
  4. customwas separated by high pressure liquid chromatography on silica using 1% methanol in dichloromethane as eluant
  5. customEvaporation of the fractions
  6. additioncontaining the major bond

Sources & evidence

ORD record
ord-60bccf60e2c240ad940e0145b5c74ec8
Source dataset
uspto-grants-1987_04
Patent number
US04657929

Reaction notes

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