Phosphorus oxychloride → 1-[1-(4-Chlorophenyl)cyclobutyl]-7-methoxy-3,4-dihydroisoquinoline

HRID 1850865Notes

Reaction equation

HRID 1850865 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:12]([NH:14][CH2:15][CH2:16][C:17]3[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=3)=O)[CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.P(Cl)(Cl)(Cl)=O>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:12]3[C:22]4[C:17](=[CH:18][CH:19]=[C:20]([O:23][CH3:24])[CH:21]=4)[CH2:16][CH2:15][N:14]=3)[CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 604097221-(4-Chlorophenyl)-N-[2-(4-methoxyphenyl)ethyl]cyclobutanecarboxamide

Product 1

HCID 668686991-[1-(4-Chlorophenyl)cyclobutyl]-7-methoxy-3,4-dihydroisoquinoline

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

1-(4-Chlorophenyl)-N-[2-(4-methoxyphenyl)ethyl]cyclobutanecarboxamide (10.58 g, 30.8 mmol) was treated with toluene (100 mL). Phosphoryl trichloride (4.72 g, 30.8 mmol) was added and the reaction mixture was heated under reflux for 8 h. After cooling to room temperature the reaction mixture was concentrated in vacuo and then slowly poured in ice water. Ethyl acetate was added and the organic layer was washed with water (2×), dried (MgSO4) and concentrated in vacuo to give an orange oil. Yield: 10.25 g.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureunder reflux for 8 h
  3. concentrationwas concentrated in vacuo
  4. additionslowly poured in ice water
  5. additionEthyl acetate was added
  6. washthe organic layer was washed with water (2×)
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated in vacuo
  9. customto give an orange oil

Sources & evidence

ORD record
ord-ce8f1dd75fe04c46b1a05344fcb0709a
Source dataset
uspto-grants-2015_02
Patent number
US08957089B2

Reaction notes

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