Octanoyl chloride → (R)-N-Octanoyl-1-phenylethylamine
Reaction equation
[C:1]1([C@H:7]([NH2:9])[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[C:17](Cl)(=[O:25])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]>C1(C)C=CC=CC=1>[C:17]([NH:9][C@@H:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[CH3:8])(=[O:25])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A solution of 50.0 g (412.6 mmol) of (R)-1-phenylethylamine and 41.75 g (412.6 mmol) of triethylamine in 750 ml of toluene was cooled to 0° C., and 73.85 g (453.9 mmol) of octanoyl chloride was added dropwise thereto. After completion of the addition, the reaction was allowed to proceed at room temperature for 3 hours. The reaction mixture was again cooled to 0° C. and then the reaction was terminated by addition of 200 ml of 10% hydrochloric acid. The toluene phase was separated, washed with 300 ml of a 10% aqueous solution of sodium hydroxide, and dried over anhydrous sodium sulfate. The solvent was then distilled off, and the residue was quantitated by HPLC. Thus was obtained 19.81 g (97%) of the title compound.
Workup
- additionAfter completion of the addition
- customthe reaction was terminated by addition of 200 ml of 10% hydrochloric acid
- customThe toluene phase was separated
- washwashed with 300 ml of a 10% aqueous solution of sodium hydroxide
- dry with materialdried over anhydrous sodium sulfate
- distillationThe solvent was then distilled off
Sources & evidence
- ORD record
- ord-298bed47e06b48539f8b41d1989d0a8a
- Source dataset
- uspto-grants-2007_10
- Patent number
- US07282605B2
Reaction notes
Loading…