N-[2-(4-benzyloxy-3-methoxyphenyl)ethyl]-1-(2-methoxyphenyl)cyclopropane carboxamide → 7-Benzyloxy-6-methoxy-1-[1-(2-methoxyphenyl)cyclopropyl]-3,4-dihydroisoquinoline

HRID 440502Notes

Reaction equation

HRID 440502 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][NH:17][C:18]([C:20]2([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[O:29][CH3:30])[CH2:22][CH2:21]2)=O)=[CH:11][C:10]=1[O:31][CH3:32])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(#N)C.P(Cl)(Cl)(Cl)=O>[CH2:1]([O:8][C:9]1[CH:14]=[C:13]2[C:12]([CH2:15][CH2:16][N:17]=[C:18]2[C:20]2([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[O:29][CH3:30])[CH2:22][CH2:21]2)=[CH:11][C:10]=1[O:31][CH3:32])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 22406839N-[2-(4-benzyloxy-3-methoxyphenyl)ethyl]-1-(2-methoxyphenyl)cyclopropane carboxamide

Product 1

HCID 224068377-Benzyloxy-6-methoxy-1-[1-(2-methoxyphenyl)cyclopropyl]-3,4-dihydroisoquinoline

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 24813Phosphorus oxychlorideSolvent

Procedure

A mixture of N-[2-(4-benzyloxy-3-methoxyphenyl)ethyl]-1-(2-methoxyphenyl)cyclopropane carboxamide (30.3 g) in acetonitrile (450 ml) and phosphoryl chloride (50 ml) was heated under reflux for 80 minutes. The solvent was evaporated in vacuo below 50° C. and the residue washed with ethyl acetate and then stirred with ethyl acetate (300 ml) and ice-cold 5% aqueous ammonia solution (200 ml) for 10 minutes. The organic layer was dried over potassium carbonate and the solvent removed by evaporation to give 7-benzyloxy-6-methoxy-1-[1-(2-methoxyphenyl)cyclopropyl]-3,4-dihydroisoquinoline.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 80 minutes
  3. customThe solvent was evaporated in vacuo below 50° C.
  4. washthe residue washed with ethyl acetate
  5. dry with materialThe organic layer was dried over potassium carbonate
  6. customthe solvent removed by evaporation

Sources & evidence

ORD record
ord-012252c1eb4d457ba352adbf047c67e8
Source dataset
uspto-grants-1996_05
Patent number
US05519034

Reaction notes

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