(Chloromethyl)cyclopropane → 3-Acetyl-N-(cyclpropylmethyl)morphinan

HRID 1758504Notes

Reaction equation

HRID 1758504 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(=O)(O)[O-].[Na+].[CH:26]1([CH2:29]Cl)[CH2:28][CH2:27]1>CN(C)C=O>[CH:26]1([CH2:29][N:15]2[CH2:16][CH2:17][C@@:6]34[C:5]5[CH:4]=[C:3]([C:18](=[O:20])[CH3:19])[CH:2]=[CH:1][C:14]=5[CH2:13][C@@H:12]2[C@@H:11]3[CH2:10][CH2:9][CH2:8][CH2:7]4)[CH2:28][CH2:27]1

Participants

5

Reactant 3

HCID 80013(Chloromethyl)cyclopropaneHCID 516892Sodium BicarbonateHCID 13100586HCID 13100586, compound

Product 1

HCID 54918993-Acetyl-N-(cyclpropylmethyl)morphinanYield 83.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 0.8 g of (-)-1-(morphinan-3-yl)-ethanone, 0.6 g of sodium bicarbonate and 10 ml dimethylformamide, was added 0.3 g of cyclopropylmethyl chloride. After the mixture had been heated at reflux for 18 hours, it was cooled to room temperature and filtered. The filtrate was concentrated under reduced pressure and the residue was dissolved in 60 ml ether. The ether solution was washed with water, dried over magnesium sulfate and removal of the solvent gave 0.8 g (83%) of crude (-)-1-[N-(cyclopropylmethyl)morphinan-3-yl]ethanone. For analysis, a sample of this compound was distilled, bp 185°-195° (0.1 mm), [α]25D-83.21° (c 1.02, MeOH).

Workup

  1. temperatureAfter the mixture had been heated
  2. temperatureat reflux for 18 hours
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. dissolutionthe residue was dissolved in 60 ml ether
  6. washThe ether solution was washed with water
  7. dry with materialdried over magnesium sulfate and removal of the solvent

Sources & evidence

ORD record
ord-b0fc39813b9e4326a079a76273774dbd
Source dataset
uspto-grants-1983_02
Patent number
US04374139

Reaction notes

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