Ethyl Acetate → 2-(4-Fluorophenyl)-6-methoxy-1-{4-(phenylmethoxy)benzyl}-1,2,3,4-tetrahydroisoquinoline

HRID 2119453Notes

Reaction equation

HRID 2119453 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH2:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([O:34][CH3:35])[CH:29]=2)[C:9](=O)[CH2:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:13][CH:12]=2)=[CH:4][CH:3]=1.C(OCC)(=O)C>P(Cl)(Cl)(Cl)=O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:26][CH2:27][C:28]3[C:33](=[CH:32][CH:31]=[C:30]([O:34][CH3:35])[CH:29]=3)[CH:9]2[CH2:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:13][CH:12]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 8857Ethyl AcetateHCID 23440755N-(4-Fluorophenyl)-N-{2-(3-methoxyphenyl)ethyl}-2-{4-(phenylmethoxy)phenyl}acetamide

Product 1

HCID 234408752-(4-Fluorophenyl)-6-methoxy-1-{4-(phenylmethoxy)benzyl}-1,2,3,4-tetrahydroisoquinolineYield 80%

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

A solution of N-(4-fluorophenyl)-N-{2-(3-methoxyphenyl)ethyl}-2-{4-(phenylmethoxy)phenyl}acetamide (6.0 g, 12.8 mmol) in phosphorous oxychloride (130 mL) under nitrogen was heated to 80° C. After 20 hours, the reaction was cooled to RT and very slowly poured over ice with vigorous stirring. Ethyl acetate (500 mL) was then added and the layers were separated. The organic layer was washed with brine, dried over MgSO4, filtered and concentrated to provide the title compound (4.61 g, 80% yield): ES−MS (m/z) 452 [M+H]+.

Workup

  1. additionvery slowly poured over ice with vigorous stirring
  2. customthe layers were separated
  3. washThe organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-b9842e1f1bfc47249047a5d7c6e31f11
Source dataset
uspto-grants-2004_02
Patent number
US06686351B2

Reaction notes

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