Water → 6-[(3-Fluorophenyl)methoxy]-1,2,3,4-tetrahydroisoquinoline

HRID 2415448Notes

Reaction equation

HRID 2415448 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][CH:20]=1)[CH2:5][O:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[C:13](=O)[NH:12][CH2:11][CH2:10]2.[H-].[Al+3].[Li+].[H-].[H-].[H-].O>O1CCCC1>[F:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][CH:20]=1)[CH2:5][O:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[CH2:13][NH:12][CH2:11][CH2:10]2

Participants

5

Reactant 3

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 226419086-[(3-Fluorophenyl)methoxy]-3,4-dihydroisoquinolin-1(2H)-one

Product 1

HCID 226418956-[(3-Fluorophenyl)methoxy]-1,2,3,4-tetrahydroisoquinoline

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 6-(3-fluoro-benzyloxy)-3,4-dihydro-2H-isoquinolin-1-one (1.2 g, 4.423 mmol) and lithium aluminum hydride (0.337 g, 8,84 mmol) in tetrahydrofuran (24 ml) was heated to 60° C. for 8 h. Water was added and an 15% aqueous solution of sodium hydroxide and the mixture was extracted with ethylacetate. After drying of the organic layer with MgSO4, filtration and evaporation, an oil was obtained (1.14 g, 99%). MS: m/e 258.0 (M+H+).

Workup

  1. extractionan 15% aqueous solution of sodium hydroxide and the mixture was extracted with ethylacetate
  2. dry with materialAfter drying of the organic layer with MgSO4, filtration and evaporation
  3. customan oil was obtained (1.14 g, 99%)

Sources & evidence

ORD record
ord-d1b0945d0dd242d1a66d63c50ca1cd32
Source dataset
uspto-grants-2004_11
Patent number
US06818774B2

Reaction notes

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