Hydrochloric Acid → HCID 13281980, compound

HRID 26471Notes

Reaction equation

HRID 26471 reaction equation
[CH3:1][N:2]1[C:11](=[O:12])[CH2:10][C@@:9]2([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C@@H:4]([CH2:5][CH2:6][CH2:7][CH2:8]2)[C:3]1=[O:19].C[O-].[Na+].Cl>CO>[CH3:1][N:2]1[C:11](=[O:12])[CH2:10][C@@:9]2([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C@H:4]([CH2:5][CH2:6][CH2:7][CH2:8]2)[C:3]1=[O:19]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10942334Sodium MethoxideHCID 71365859(4aR,8aR)-2-Methyl-4a-phenylhexahydroisoquinoline-1,3(2H,4H)-dione

Product 1

HCID 13281980HCID 13281980, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

N-Methyl-4a-phenyl-1,3-diketo-trans-decahydroisoquinoline (2.0 g) in 100 ml of methanol was treated with 400 mg of sodium methoxide and the mixture was refluxed for 30 minutes. It was allowed to stand overnight at 25°, then poured into 1 N hydrochloric acid and extracted with ether. The ether extracts were washed successively with water and brine, then dried (MgSO4) and the ether evaporated to yield 1.9 g of an oil. NMR (CDCl3): methylene envelope from 70 to 140 cps (8H); singlet at 177 cps (3H); multiplet at 145 to 205 cps (3H); singlet at 434 cps (5H).

Workup

  1. temperaturethe mixture was refluxed for 30 minutes
  2. extractionextracted with ether
  3. washThe ether extracts were washed successively with water and brine
  4. dry with materialdried (MgSO4)
  5. customthe ether evaporated

Sources & evidence

ORD record
ord-3515ee8009ed4b9eb559354014df1976
Source dataset
uspto-grants-1979_04
Patent number
US04150135

Reaction notes

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