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ChemicalBook CAS DataBase List 7-(Benzyloxy)-1,2,3,4-tetrahydroisoquinoline
152035-13-7

7-(Benzyloxy)-1,2,3,4-tetrahydroisoquinoline synthesis

4synthesis methods
Isoquinoline, 7-(phenylmethoxy)-

158984-80-6
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7-(Benzyloxy)-1,2,3,4-tetrahydroisoquinoline

152035-13-7
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Yield:152035-13-7 64%

Reaction Conditions:

in methanol;diethyl ether;hexane;

Steps:

29.2 7-Benzyloxy-1,2,3,4-tetrahydroisoquinoline

Step 2 7-Benzyloxy-1,2,3,4-tetrahydroisoquinoline 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 crystallized 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).

References:

US5700809,1997,A