Formaldehyde → HCID 68134002, compound

HRID 268289Notes

Reaction equation

HRID 268289 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([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:5][CH:4]=1.[CH2:21]=O>>[ClH:2].[Cl:2][C:3]1[CH:4]=[CH:5][C:6]([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:7][CH:8]=1

Participants

3

Reactant 2

HCID 712FormaldehydeHCID 21551810HCID 21551810, compound

Product 1

HCID 68134002HCID 68134002, compound

Procedure

The free base isolated from 1.55 g. of rac.- 4-(4-chlorophenyl)-1,2,3,4-tetrahydro-7-methoxyisoquinoline hydrochloride is shaken with 1.1 ml. of a 35% formaldehyde solution and the mixture is allowed to stand at room temperature for 2 hours. It is hydrogenated over 1 g. of Raney nickel, filtered from the catalyst, the filtrate is evaporated and the residue is crystallized with ethanolic hydrogen chloride, methanol and ether. Recrystallization from methanol-ether gives rac.-4-(4-chlorophenyl)-1,2,3,4-tetrahydro-7-methoxy-2-methylisoquinoline hydrochloride, m.p. 244°-146°.

Workup

  1. customThe free base isolated from 1.55 g
  2. filtrationof Raney nickel, filtered from the catalyst
  3. customthe filtrate is evaporated
  4. customthe residue is crystallized with ethanolic hydrogen chloride, methanol and ether
  5. customRecrystallization from methanol-ether

Sources & evidence

ORD record
ord-74ab1b1630fd45918bb2f739f4b7b07e
Source dataset
uspto-grants-1976_03
Patent number
US03947456

Reaction notes

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