Hydrochloric Acid → 2,8a-dibenzyl-1,2,3,4,8,8a-hexahydroisoquinolin-6(7H)-one

HRID 1042322Notes

Reaction equation

HRID 1042322 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11](=O)[CH:10]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[O-].[Na+].[CH3:25][C:26]([CH:28]=[CH2:29])=[O:27].Cl>CO>[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]2[C:10]([CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)([CH2:29][CH2:28][C:26](=[O:27])[CH:25]=2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6570Methyl vinyl ketoneHCID 10942334Sodium MethoxideHCID 230036591,3-Dibenzylpiperidin-4-one

Product 1

HCID 444429102,8a-dibenzyl-1,2,3,4,8,8a-hexahydroisoquinolin-6(7H)-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1,3-Dibenzylpiperidin-4-one (3, R1B=H, Z=benzyl) (3.98 g, 13.96 mmol) was added to a solution of sodium methoxide (0.83 g, 15.36 mmol) in 80 mL of methanol and stirred at ambient temperature for 45 min. The contents were cooled to 0° C. and methylvinyl ketone (1.74 mL, 20.94 mmol) was added over 30 min. The contents were allowed to warm to ambient temperature and stir for 18 h. Concentrated HCl (1.55 mL) was added, the contents were stirred for a further 5 min and the solvents were evaporated to give a brown oil which was triturated in diethyl ether to give the title compound, 1.90 g. LC-MS: RT=2.26 min. (M+H)+ 332.

Workup

  1. temperatureThe contents were cooled to 0° C.
  2. temperatureto warm to ambient temperature
  3. stirringstir for 18 h
  4. stirringthe contents were stirred for a further 5 min
  5. customthe solvents were evaporated
  6. customto give a brown oil which
  7. customwas triturated in diethyl ether

Sources & evidence

ORD record
ord-78622167dabc420eae04c95e2ab3355b
Source dataset
uspto-grants-2013_10
Patent number
US08557839B2

Reaction notes

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