7-(Benzyloxy)isoquinoline → 7-(Benzyloxy)-1,2,3,4-tetrahydroisoquinoline

HRID 1940568

Reaction equation

HRID 1940568 reaction equation
[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([CH:13]=[CH:14][N:15]=[CH:16]2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CO.[Pt]=O>[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([CH2:13][CH2:14][NH:15][CH2:16]2)=[CH:11][CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 211924457-(Benzyloxy)isoquinoline

Product 1

HCID 214630147-(Benzyloxy)-1,2,3,4-tetrahydroisoquinolineYield 64%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 887MethanolSolvent

Procedure

7-Benzyloxyisoquinoline (1.5 g, 6.37 mmol) in methanol (100 ml) was hydrogenated at 50 psi on a Parr apparatus using platinum oxide (100 mg) as catalyst. The catalyst was collected by filtration, the filtrate evaporated under reduced pressure to give an oil which crystallised on treatment with hexane/diethyl ether to give the title compound (0.96 g, 64%); δH (CDCl3) 2.72 (2H, t, J 6 Hz, CH2), 3.11 (2H, t, J 6 Hz, CH2), 3.90 (2H, s, CH2), 6.62 (1H, d, J 2.25 Hz, tetrahydroisoquinolinyl H), 6.78 (1H, dd, J 5.75, 2.75 Hz, tetrahydroisoquinolinyl H), 6.99 (1H, d, J 9.25 Hz, tetrahydroisoquinolinyl H), and 7.25-7.43 (5H, m, ArH).

Workup

  1. filtrationThe catalyst was collected by filtration
  2. customthe filtrate evaporated under reduced pressure
  3. customto give an oil which
  4. customcrystallised on treatment with hexane/diethyl ether

Sources & evidence

ORD record
ord-3201db18bb334fb4a3e432ad9fa7efd5
Source dataset
uspto-grants-1997_12
Patent number
US05700809

Linked notes

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