Phosphorus oxychloride → 1-[(3,4-Dimethoxyphenyl)methyl]-6,7-dimethoxy-3,4-dihydroisoquinoline--hydrogen chloride (1/1)

HRID 1490324Notes

Reaction equation

HRID 1490324 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:22]=[CH:23][C:24]=1[O:25][CH3:26])[CH2:6][CH2:7][NH:8][C:9](=O)[CH2:10][C:11]1[CH:16]=[C:15]([O:17][CH3:18])[C:14]([O:19][CH3:20])=[CH:13][CH:12]=1.P(Cl)(Cl)([Cl:29])=O>C(#N)C>[ClH:29].[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:22]=[CH:23][C:24]=1[O:25][CH3:26])[CH2:6][C:7]1[C:12]2[C:11](=[CH:16][C:15]([O:17][CH3:18])=[C:14]([O:19][CH3:20])[CH:13]=2)[CH2:10][CH2:9][N:8]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 67318N-(3,4-Dimethoxyphenethyl)-2-(3,4-dimethoxyphenyl)acetamide

Product 1

HCID 123172411-[(3,4-Dimethoxyphenyl)methyl]-6,7-dimethoxy-3,4-dihydroisoquinoline--hydrogen chloride (1/1)

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 570 g of N-(3,4-dimethoxyphenethyl)-2-(4,5-dimethoxyphenyl)acetamide and 500 ml of phosphorus oxychloride in 3500 ml of acetonitrile was heated under reflux for 0.5 hour. The solvent was evaporated, and ethanol was added to the residue, followed by allowing to stand. The thus precipitated crystal was collected by filtration to yield 590 g of the titled compound.

Workup

  1. temperatureunder reflux for 0.5 hour
  2. customThe solvent was evaporated
  3. additionethanol was added to the residue
  4. filtrationThe thus precipitated crystal was collected by filtration

Sources & evidence

ORD record
ord-8952c3f2ff50427f87b1485e6695e485
Source dataset
uspto-grants-1997_10
Patent number
US05681954

Reaction notes

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