Formaldehyde → 4-(3,4-Dichlorophenyl)-7-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline--hydrogen chloride (1/1)

HRID 268295Notes

Reaction equation

HRID 268295 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]([CH:10]2[C:19]3[C:14](=[CH:15][C:16]([O:20][CH3:21])=[CH:17][CH:18]=3)[CH2:13][NH:12][CH2:11]2)[CH:6]=[CH:7][C:8]=1[Cl:9].[CH2:22]=O>[Ni].CO>[ClH:2].[Cl:2][C:3]1[CH:4]=[C:5]([CH:10]2[C:19]3[C:14](=[CH:15][C:16]([O:20][CH3:21])=[CH:17][CH:18]=3)[CH2:13][N:12]([CH3:22])[CH2:11]2)[CH:6]=[CH:7][C:8]=1[Cl:9]

Participants

5

Reactant 2

HCID 712FormaldehydeHCID 68134283HCID 68134283, compound

Product 1

HCID 1574894-(3,4-Dichlorophenyl)-7-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline--hydrogen chloride (1/1)

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

The free base prepared from 5.20 g. of rac.-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-7-methoxyisoquinoline hydrochloride is stirred at room temperature with 75 ml. of methanol and 3.8 ml. of 35% formaldehyde solution for 2 hours and thereupon hydrogenated over 2 g. of Raney nickel. After filtering off, evaporation, acidification with ethanolic hydrogen chloride, crystallization and recrystallization from methanol-ether, there is obtained rac.-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-7-methoxy-2-methylisoquinoline hydrochloride, m.p. 273°-275°.

Workup

  1. customThe free base prepared from 5.20 g
  2. filtrationAfter filtering off
  3. customevaporation, acidification
  4. customwith ethanolic hydrogen chloride, crystallization and recrystallization from methanol-ether

Sources & evidence

ORD record
ord-70f3f281d9054c5b8d8b048730518bb9
Source dataset
uspto-grants-1976_03
Patent number
US03947456

Reaction notes

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