HCID 45263090, compound → 8-Phenyl-1,2,3,4-tetrahydroisoquinoline hydrochloride

HRID 27247Notes

Reaction equation

HRID 27247 reaction equation
[ClH:1].C([N:9]1[CH2:18][CH2:17][C:16]2[C:11](=[C:12]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH:13]=[CH:14][CH:15]=2)[CH2:10]1)C1C=CC=CC=1>[Pd].C(O)C>[ClH:1].[C:19]1([C:12]2[CH:13]=[CH:14][CH:15]=[C:16]3[C:11]=2[CH2:10][NH:9][CH2:18][CH2:17]3)[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

4

Reactant 1

HCID 45263090HCID 45263090, compound

Product 1

HCID 452657048-Phenyl-1,2,3,4-tetrahydroisoquinoline hydrochloride

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 6.20 parts of 2-benzyl-8-phenyl-1,2,3,4-tetrahydroisoquinoline hydrochloride and 0.62 parts of 5% palladium-on-carbon catalyst in 100 parts by volume of ethanol is hydrogenated at 2 psi and ambient temperature for about 6 hours. The filtered reaction solution is concentrated to 75 parts by volume and after the addition of ether crystalline solid is formed. This solid is recrystallized from ethanol to yield 8-phenyl-1,2,3,4-tetrahydroisoquinoline hydrochloride, as white crystals melting at about 268°-270° C. This compound has the following formula ##STR17##

Workup

  1. customThe filtered reaction solution
  2. concentrationis concentrated to 75 parts by volume
  3. additionafter the addition of ether crystalline solid
  4. customis formed
  5. customThis solid is recrystallized from ethanol

Sources & evidence

ORD record
ord-63e525c625584e91b3679d9e3bb16686
Source dataset
uspto-grants-1980_09
Patent number
US04220778

Reaction notes

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