Formaldehyde → HCID 15113388, compound

HRID 1763900Notes

Reaction equation

HRID 1763900 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:8][NH:9][CH2:10]2)=[CH:5][CH:4]=1.[CH2:19]=O>CO.[Ni]>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]([C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH2:8][N:9]([CH3:19])[CH2:10]2)=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 712FormaldehydeHCID 13072903HCID 13072903, compound

Product 1

HCID 15113388HCID 15113388, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

(+)- 7 -methoxy- 4 -phenyl- 1,2,3,4 tetrahydroisoquinoline (2.4 g) was dissolved in methanol (50 ml) and 35% formaldehyde solution (3 ml) was added. The solution was stirred at ambient temperature for two hours when Raney nickel (1 g) was added and the solution hydrogenated at Atmospheric Pressure. The catalyst was removed by filtration, washed with ethanol and the filtrate and washings evaporated under reduced pressure to give the title compound as a colourless oil. Treatment of the title compound with ethereal hydrogen chloride gave its hydrochloride salt (2.3 g), m.p. 242° - 3° C. (dec) (methanol-ether) [α]D25 + 21.8° (water).

Workup

  1. additionwas added
  2. customThe catalyst was removed by filtration
  3. washwashed with ethanol
  4. customthe filtrate and washings evaporated under reduced pressure

Sources & evidence

ORD record
ord-6b7c50bc636545c0bb1f632aad502891
Source dataset
uspto-grants-1978_09
Patent number
US04113869

Reaction notes

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