Phosphorus oxychloride → HCID 22406737, compound

HRID 440525Notes

Reaction equation

HRID 440525 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][NH:11][C:12]([C:14]2([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[Cl:24])[CH2:17][CH2:16][CH2:15]2)=O)=[CH:5][C:4]=1[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.P(Cl)(Cl)(Cl)=O>C(#N)C>[Cl:24][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[C:14]1([C:12]2[C:7]3[C:6](=[CH:5][C:4]([C:25]4[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=4)=[C:3]([O:2][CH3:1])[CH:8]=3)[CH2:9][CH2:10][N:11]=2)[CH2:15][CH2:16][CH2:17]1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 22406772HCID 22406772, compound

Product 1

HCID 22406737HCID 22406737, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of N-[2-(2-methoxy-5-biphenylyl)ethyl]-1-(2-chlorophenyl)cyclobutane carboxamide (12.5 g, prepared as described in Example E30), phosphorus oxychloride (25 ml) and acetonitrile (150 ml) was heated under reflux for 6 hours. The solvent was removed by distillation and the residue added to a mixture of ice and water. The mixture was extracted with dichloromethane to yield a solid which was recrystallised from propan-2-ol to give 1-[1-(2-chlorophenyl)cyclobutyl]-7-methoxy-6-phenyl-3,4-dihydroisoquinoline, m.p. 149°-152° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 6 hours
  3. customThe solvent was removed by distillation
  4. additionthe residue added to a mixture of ice and water
  5. extractionThe mixture was extracted with dichloromethane
  6. customto yield a solid which
  7. customwas recrystallised from propan-2-ol

Sources & evidence

ORD record
ord-964ad55f0a914e05ae5692aec6dc1e9a
Source dataset
uspto-grants-1996_05
Patent number
US05519034

Reaction notes

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