Phosphorus oxychloride → 1-(N-benzyloxycarbonyl-p-chloroanilinomethyl)-6,7-dibenzyloxy-3,4-dihydroisoquinoline

HRID 27169Notes

Reaction equation

HRID 27169 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH2:23][CH2:24][NH:25][C:26](=O)[CH2:27][N:28]([C:36]([O:38][CH2:39]C2C=CC=CC=2)=[O:37])[C:29]2[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=2)[CH:12]=[CH:13][C:14]=1[O:15][CH2:16]C1C=CC=CC=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.P(Cl)(Cl)(Cl)=O>C1C=CC=CC=1>[CH2:39]([O:38][C:36]([N:28]([CH2:27][C:26]1[C:12]2[C:11](=[CH:10][C:9]([O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[C:14]([O:15][CH2:16][C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:13]=2)[CH2:23][CH2:24][N:25]=1)[C:29]1[CH:30]=[CH:31][C:32]([Cl:35])=[CH:33][CH:34]=1)=[O:37])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 20460555N-[2-(3,4-dibenzyloxyphenyl)ethyl]-2-(N-benzyloxycarbonyl-p-chloroanilino)acetamide

Product 1

HCID 204605211-(N-benzyloxycarbonyl-p-chloroanilinomethyl)-6,7-dibenzyloxy-3,4-dihydroisoquinolineYield 197.4%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of N-[2-(3,4-dibenzyloxyphenyl)ethyl]-2-(N-benzyloxycarbonyl-p-chloroanilino)acetamide (7.3 g), phosphorus oxychloride (2.3 g) and anhydrous benzene (73 ml) was refluxed for four hours. The reaction mixture was concentrated to dryness under reduced pressure and to the residue was added a diluted aqueous ammonia solution, and then the mixture was extracted with ethyl acetate. The extract was washed with water and dried, and the solvent was distilled off to give 1-(N-benzyloxycarbonyl-p-chloroanilinomethyl)-6,7-dibenzyloxy-3,4-dihydroisoquinoline (7.0 g).

Workup

  1. temperaturewas refluxed for four hours
  2. concentrationThe reaction mixture was concentrated to dryness under reduced pressure and to the residue
  3. additionwas added a diluted aqueous ammonia solution
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe extract was washed with water
  6. customdried
  7. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-4f917a42480549e380d379e58e02f6e1
Source dataset
uspto-grants-1980_09
Patent number
US04220647

Reaction notes

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