Dimethylamine → 4-Fluoro-N,N-dimethyl-γ-oxobenzenebutanamide
Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:14])[CH2:9][CH2:10][C:11](O)=[O:12])=[CH:4][CH:3]=1.[CH3:15][NH:16][CH3:17]>O1CCCC1>[CH3:15][N:16]([CH3:17])[C:11](=[O:12])[CH2:10][CH2:9][C:8](=[O:14])[C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 30.5 g (0.155 Mol) of 4-fluoro-γ-oxobenzenebutanoic acid in 470 ml tetrahydrofuran, 35.0 g (0.216 Mol) of N,N′-carbonyldiimidazole was added with stirring and at room temperature and held at room temperature for a further 2.5 hours. Then, 13.7 g (0.304 Mol) of dimethylamine was added under strong external cooling by means of an ice-ethanol mixture. After the mixture had stood at room temperature for 12 hours, the solvent was removed in vacuo, the residue was divided between dichloromethane and 10% aqueous citric acid solution, the organic phase was dried over sodium sulphate and once again evaporated down in vacuo. After purification by column chromatography (eluant:ethyl acetate) on silica gel the crude product yielded 30.22 g (87% of theory) of colourless crystals of Rf=0.31 (eluant:ethyl acetate/glacial acetic acid 99.99/0.01).
Workup
- waitAfter the mixture had stood at room temperature for 12 hours
- customthe solvent was removed in vacuo
- dry with materialthe organic phase was dried over sodium sulphate
- customonce again evaporated down in vacuo
- customAfter purification by column chromatography (eluant:ethyl acetate) on silica gel the crude product
- customyielded 30.22 g (87% of theory) of colourless crystals of Rf=0.31 (eluant:ethyl acetate/glacial acetic acid 99.99/0.01)
Sources & evidence
- ORD record
- ord-6be8b56fd9e14b818339871c69e0b549
- Source dataset
- uspto-grants-2009_03
- Patent number
- US07498325B2
Reaction notes
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