Methanol → N-[2-(3,4-dimethoxyphenyl)ethyl]-3-[4-(trifluoromethyl)phenyl]propanamide

HRID 888000Notes

Reaction equation

HRID 888000 reaction equation
CO[C:3](=[O:16])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]([F:15])([F:14])[F:13])=[CH:8][CH:7]=1.[CH3:17][O:18][C:19]1[CH:20]=[C:21]([CH2:27][CH2:28][NH2:29])[CH:22]=[CH:23][C:24]=1[O:25][CH3:26].C[O-].[Na+].CO>C1(C)C=CC=CC=1>[CH3:17][O:18][C:19]1[CH:20]=[C:21]([CH2:27][CH2:28][NH:29][C:3](=[O:16])[CH2:4][CH2:5][C:6]2[CH:7]=[CH:8][C:9]([C:12]([F:13])([F:14])[F:15])=[CH:10][CH:11]=2)[CH:22]=[CH:23][C:24]=1[O:25][CH3:26]

Participants

6

Reactant 4

HCID 887MethanolHCID 8421HomoveratrylamineHCID 10942334Sodium MethoxideHCID 11977307Methyl 4-(trifluoromethyl)benzenepropanoate

Product 1

HCID 27282117N-[2-(3,4-dimethoxyphenyl)ethyl]-3-[4-(trifluoromethyl)phenyl]propanamide

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

3-(4-trifluoromethyl-phenyl)-propionic acid methyl ester is dissolved in toluene, 1.05 equivalents 2-(3,4-dimethoxy-phenyl)-ethylamine (commercially available) and 1.1 equivalents sodium methoxide (30% in methanol) are added. At normal pressure the reaction mixture is heated to a maximum of 110° C. and methanol distilled until full conversion is reached. The reaction mixture is washed with water and sulfuric acid. During cooling of the organic phase, the compound 3 crystallises and is filtered, washed with cold toluene and dried in vacuo at 50° C.

Workup

  1. distillationdistilled until full conversion
  2. washThe reaction mixture is washed with water and sulfuric acid
  3. temperatureDuring cooling of the organic phase
  4. customthe compound 3 crystallises
  5. filtrationis filtered
  6. washwashed with cold toluene
  7. customdried in vacuo at 50° C.

Sources & evidence

ORD record
ord-851e5e031a4d454f99390ac6f486f396
Source dataset
uspto-grants-2012_08
Patent number
US08247560B2

Reaction notes

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