Sodium Hydroxide → 5-(Tetrahydropyran-2-yloxy)-1,2,3,4-tetrahydroisoquinoline

HRID 1416357Notes

Reaction equation

HRID 1416357 reaction equation
[OH-].[Na+].[O:3]1[CH2:8][CH2:7][CH2:6][CH2:5][CH:4]1[O:9][C:10]1[CH:19]=[CH:18][CH:17]=[C:16]2[C:11]=1[CH2:12][CH2:13][N:14](C(=O)C(F)(F)F)[CH2:15]2>O1CCOCC1.ClCCl>[O:3]1[CH2:8][CH2:7][CH2:6][CH2:5][CH:4]1[O:9][C:10]1[CH:19]=[CH:18][CH:17]=[C:16]2[C:11]=1[CH2:12][CH2:13][NH:14][CH2:15]2

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 154342975-(Tetrahydropyran-2-yloxy)-2-trifluoroacetyl-1,2,3,4-tetrahydroisoquinolin

Product 1

HCID 109005345-(Tetrahydropyran-2-yloxy)-1,2,3,4-tetrahydroisoquinoline

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

Excess of 2 mol L-1 aqueous sodium hydroxide was added to a solution of 5-(tetrahydropyran-2-yloxy)-2-trifluoroacetyl-1,2,3,4-tetrahydroisoquinoline (Example 3) (4.1 g, 12.4 mmol) in dioxane. The mixture was stirred overnight, diluted with dichloromethane, washed with water and aqueous sodium chloride and evaporated. Yield 2.77 g, 96% 1H NMR (CDCl3, 400 MHz): 7.07 (1H, t, 8.1 Hz), 6.92 (1H, d, 8.3 Hz), 6.66 (1H, d, 7.6 Hz), 5.43 (1H, t, 3.2 Hz), 3.99 (2H, s), 3.76 (1H, m), 3.61 (1H, m), 3.14 (2H, t, 6.1 Hz), 2,73 (2H, m), 1.5-2.1 (6H, m); 13C NMR (CDCl3, 100 MHz): 154.6, 137.2, 126.0, 124.3, 119.1, 111.2, 95.8, 61.9, 48.3, 43.7, 30.5, 25.2, 23.5, 18.9; MS (EI, 70 eV): 233 (M+, 8%), 148 (92%), 132 (23%), 120 (47%), 91 (16%), 85 (100%).

Workup

  1. washwashed with water and aqueous sodium chloride
  2. customevaporated

Sources & evidence

ORD record
ord-5d10ceb26b634679b9ef9962e158c064
Source dataset
uspto-grants-1999_06
Patent number
US05912342

Reaction notes

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