Methanol → HCID 20534452, compound

HRID 1156988Notes

Reaction equation

HRID 1156988 reaction equation
[C:1]1([C:7]23[CH2:15][CH2:14][CH2:13][CH:12]2[CH2:11][NH:10][CH2:9][CH2:8]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CO.C(=O)([O-])[O-].[K+].[K+].[C:24]1([CH2:30][C:31](Cl)=[O:32])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>O>[C:1]1([C:7]23[CH2:15][CH2:14][CH2:13][CH:12]2[CH:11]([C:31](=[O:32])[CH2:30][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[NH:10][CH2:9][CH2:8]3)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 7679Phenylacetyl chlorideHCID 11430Potassium CarbonateHCID 20534426HCID 20534426, compound

Product 1

HCID 20534452HCID 20534452, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

To a cold solution (0°-5° C.) of 3.0 g. of 4a-phenyl-2,3,4,4a,5,6,7,7a-octahydro-1H-2-pyrindine in 47 ml. of methanol containing 14 ml. of water and 2.6 g. of potassium carbonate was added 2.6 g. of phenylacetyl chloride in one portion. The reaction mixture was stirred at 0°-5° C. for thirty minutes and then was warmed to 25° C., at which it was stirred for an additional one hour. The reaction mixture was concentrated under reduced pressure, leaving an oily residue. The oil was then dissolved in 500 ml. of diethyl ether and washed with dilute aqueous sodium bicarbonate solution and with water. After drying the ethereal solution, the solvent was evaporated under reduced pressure to afford 4a-phenyl-2-phenylacetyl-2,3,4,4a,5,6,7,7a-octahydro-1H-2-pyrindine formed in the above acylation reaction as an oil.

Workup

  1. customTo a cold solution (0°-5° C.) of 3.0 g
  2. stirringwas stirred for an additional one hour
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. customleaving an oily residue
  5. dissolutionThe oil was then dissolved in 500 ml
  6. washof diethyl ether and washed with dilute aqueous sodium bicarbonate solution and with water
  7. customAfter drying the ethereal solution
  8. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-0fe059685e5146cabb3c7425ed887185
Source dataset
uspto-grants-1982_06
Patent number
US04337341

Reaction notes

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