Hydrochloric Acid → HCID 22406853, compound

HRID 440498Notes

Reaction equation

HRID 440498 reaction equation
Cl.C([O:9][C:10]1[CH:19]=[C:18]2[C:13]([CH2:14][CH2:15][N:16]([CH3:35])[CH:17]2[C:20]2([C:24]3[CH:29]=[CH:28][C:27]([O:30][C:31]([F:34])([F:33])[F:32])=[CH:26][CH:25]=3)[CH2:23][CH2:22][CH2:21]2)=[CH:12][C:11]=1[O:36][CH3:37])C1C=CC=CC=1.Cl.[C:39]([OH:44])(=[O:43])[C:40]([OH:42])=[O:41]>>[C:39]([OH:44])(=[O:43])[C:40]([OH:42])=[O:41].[OH:9][C:10]1[CH:19]=[C:18]2[C:13]([CH2:14][CH2:15][N:16]([CH3:35])[CH:17]2[C:20]2([C:24]3[CH:29]=[CH:28][C:27]([O:30][C:31]([F:32])([F:33])[F:34])=[CH:26][CH:25]=3)[CH2:23][CH2:22][CH2:21]2)=[CH:12][C:11]=1[O:36][CH3:37]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 971Oxalic AcidHCID 22406802HCID 22406802, compound

Product 1

HCID 22406853HCID 22406853, compound

Procedure

A mixture of 7-benzyloxy-6-methoxy-2-methyl-1-[1-(4-trifluoromethoxyphenyl)cyclobutyl]-1,2,3,4-tetrahydroisoquinoline hydrochloride (2.94 g), industrial methylated spirits (65 ml) and concentrated hydrochloric acid (65 ml) was heated under reflux for 45 minutes. The mixture was concentrated, and dried by azeotropic distillation with propan-2-ol. The residue was dissolved in ether and treated with one equivalent of oxalic acid to yield 7-hydroxy-6-methoxy-2-methyl-1-[1-(4-trifluoromethoxyphenyl)cyclobutyl]-1,2,3,4-tetrahydroisoquinoline oxalate which was crystallised from acetonitrile.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 45 minutes
  3. concentrationThe mixture was concentrated
  4. dry with materialdried by azeotropic distillation with propan-2-ol
  5. dissolutionThe residue was dissolved in ether

Sources & evidence

ORD record
ord-ba6fabd62d4f4ab6ba267ad0239da09d
Source dataset
uspto-grants-1996_05
Patent number
US05519034

Reaction notes

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