Acrylonitrile → (-)-3-Acetyl-17-morphinanpropanenitrile

HRID 1758506Notes

Reaction equation

HRID 1758506 reaction equation
[CH:1]1[C:14]2[CH2:13][C@H:12]3[NH:15][CH2:16][CH2:17][C@:6]4([C@H:11]3[CH2:10][CH2:9][CH2:8][CH2:7]4)[C:5]=2[CH:4]=[C:3]([C:18](=[O:20])[CH3:19])[CH:2]=1.C(N(CC)CC)C.[C:28](#[N:31])[CH:29]=[CH2:30]>C(O)C>[C:18]([C:3]1[CH:2]=[CH:1][C:14]2[CH2:13][C@H:12]3[N:15]([CH2:30][CH2:29][C:28]#[N:31])[CH2:16][CH2:17][C@@:6]4([C:5]=2[CH:4]=1)[C@H:11]3[CH2:10][CH2:9][CH2:8][CH2:7]4)(=[O:20])[CH3:19]

Participants

5

Reactant 3

HCID 7855AcrylonitrileHCID 8471TriethylamineHCID 13100586HCID 13100586, compound

Product 1

HCID 13100593(-)-3-Acetyl-17-morphinanpropanenitrileYield 94.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of 1.5 g of (-)-1-(morphinan-3-yl)ethanone, 2.3 g of triethylamine and 35 ml of absolute ethanol, was added 0.35 g of acrylonitrile. After the mixture had been heated at reflux for 16 hours the solvent and excess of reagents were removed under reduced pressure to give 1.7 g (94%) of crude (-)-3-acetyl-17-morphinanpropanenitrile. For analysis, a sample of this compound was distilled, bp 220°-230° (0.05 mm), [α]25D-65.5° (c 1.03, MeOH).

Workup

  1. temperatureAfter the mixture had been heated
  2. temperatureat reflux for 16 hours the solvent
  3. customexcess of reagents were removed under reduced pressure

Sources & evidence

ORD record
ord-614549276e414c0ebbc4c35aff1e3f76
Source dataset
uspto-grants-1983_02
Patent number
US04374139

Reaction notes

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