Formaldehyde → HCID 68132626, compound

HRID 268291Notes

Reaction equation

HRID 268291 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]([CH:9]2[C:18]3[C:13](=[CH:14][C:15]([O:19][CH3:20])=[CH:16][CH:17]=3)[CH2:12][NH:11][CH2:10]2)[CH:6]=[CH:7][CH:8]=1.[CH2:21]=O>CO>[ClH:2].[Cl:2][C:3]1[CH:4]=[C:5]([CH:9]2[C:18]3[C:13](=[CH:14][C:15]([O:19][CH3:20])=[CH:16][CH:17]=3)[CH2:12][N:11]([CH3:21])[CH2:10]2)[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 712FormaldehydeHCID 68132302HCID 68132302, compound

Product 1

HCID 68132626HCID 68132626, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The free base isolated from 8.0 g. of rac.-4-(3-chlorophenyl)-1,2,3,4-tetrahydro-7-methoxyisoquinoline hydrochloride is taken up in 150 ml. of methanol, 6 ml. of a 35% formaldehyde solution are added and the mixture is shaken until the precipitate formed again completely dissolves. The mixture is thereupon hydrogenated over 6 g. of Raney nickel, filtered and, after acidification with ethanolic hydrogen chloride, crystallized. Recrystallization from methanol-ether gives rac.-4-(3-chlorophenyl)-1,2,3,4-tetrahydro-7-methoxy-2-methylisoquinoline hydrochloride, m.p. 250°-251°.

Workup

  1. customThe free base isolated from 8.0 g
  2. customformed again completely
  3. dissolutiondissolves
  4. filtrationof Raney nickel, filtered
  5. customafter acidification with ethanolic hydrogen chloride, crystallized
  6. customRecrystallization from methanol-ether

Sources & evidence

ORD record
ord-530305ceee884556af78ad6481a756e0
Source dataset
uspto-grants-1976_03
Patent number
US03947456

Reaction notes

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