Triethylamine → N-cyclopropyl-3-(4-fluorophenyl)propanamide
Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([OH:12])=O)=[CH:4][CH:3]=1.C(Cl)(=O)C(Cl)=O.[CH:19]1([NH2:22])[CH2:21][CH2:20]1.C(N(CC)CC)C>C(Cl)Cl.O.CN(C)C=O>[CH:19]1([NH:22][C:10](=[O:12])[CH2:9][CH2:8][C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)[CH2:21][CH2:20]1Participants
8
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 0 °C
Procedure
To a stirred solution of 3-(4-fluorophenyl)propionic acid (5 g, 31 mmoles) and 0.1 mL of dimethylformamide in 50 mL of anhydrous CH2Cl2 at 0° C. was added oxalyl chloride (2.84 mL, 32.6 mmoles) and the mixture was stirred for 1 hour at 0° C. and for 1 hour at room temperature. After cooling to 0° C. were added cyclopropylamine (2.6 mL, 37.2 mmoles) and triethylamine (6.5 mL, 46.5 mmoles), and the mixture was stirred for 1 hour while warming to room temperature gradually. Then water was added and the product was extracted with CH2Cl2. The extract was washed with water, dried over MgSO4 and evaporated to give a solide residue. It was recrystallized from CH2Cl2 and hexane to give 4.94 g of N-cyclopropyl-3-(4-fluorophenyl)propionamide.
Workup
- temperatureAfter cooling to 0° C.
- stirringthe mixture was stirred for 1 hour
- temperaturewhile warming to room temperature gradually
- extractionthe product was extracted with CH2Cl2
- washThe extract was washed with water
- dry with materialdried over MgSO4
- customevaporated
- customto give a solide residue
- customIt was recrystallized from CH2Cl2 and hexane
Sources & evidence
- ORD record
- ord-669fca97987a4db8868c7a78d014de78
- Source dataset
- uspto-grants-2007_11
- Patent number
- US07291744B2
Reaction notes
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