Hydrochloric Acid → (R)-N-Allyl-N-octanoyl-1-phenylethylamine

HRID 1180691Notes

Reaction equation

HRID 1180691 reaction equation
[C:1]([NH:10][C@@H:11]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH3:12])(=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[CH2:19](Br)[CH:20]=[CH2:21].[H-].[Na+].Cl>C1(C)C=CC=CC=1>[CH2:21]([N:10]([C@@H:11]([C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)[CH3:12])[C:1](=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])[CH:20]=[CH2:19]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 69501790(R)-N-Octanoyl-1-phenylethylamine

Product 1

HCID 69501896(R)-N-Allyl-N-octanoyl-1-phenylethylamineYield 86%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A solution of 10.0 g (40.0 mmol) of (R)-N-octanoyl-1-phenylethylamine in 20 ml of toluene, and 9.90 g (80.0 mmol) of allyl bromide were added to a suspension of 3.20 g (80.0 mmol) of sodium hydride (60%) in 74 ml of toluene, and the reaction was allowed to proceed at 100° C. for 6 hours. The reaction mixture was cooled to room temperature and added dropwise to 80 ml of ice-cooled 1 N hydrochloric acid to thereby terminate the reaction. The resulting mixture was extracted with three 30-ml portions of hexane. The organic phase was washed with 50 ml of water and then dried over anhydrous sodium sulfate, and the solvent was distilled off. The residue was quantitated by HPLC. Thus was obtained 9.87 g (86%) of the title compound.

Workup

  1. customto thereby terminate
  2. customthe reaction
  3. extractionThe resulting mixture was extracted with three 30-ml portions of hexane
  4. washThe organic phase was washed with 50 ml of water
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-cc2c3f9f70b24c4e8f1b3a3e184469d7
Source dataset
uspto-grants-2007_10
Patent number
US07282605B2

Reaction notes

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