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

HRID 1940568

반응식

HRID 1940568 반응식
[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

참가 물질

4

반응물 1

HCID 211924457-(Benzyloxy)isoquinoline

생성물 1

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

시약·촉매·용매 2

HCID 82844Platinum oxide (PtO)촉매HCID 887Methanol용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-3201db18bb334fb4a3e432ad9fa7efd5
출처 데이터셋
uspto-grants-1997_12
특허 번호
US05700809

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