Potassium Carbonate → 2-(3-piperidinopropyl)-4-phenyl-1(2H)-isoquinolone

HRID 1074617Notes

Reaction equation

HRID 1074617 reaction equation
Cl[CH2:2][CH2:3][CH2:4][N:5]1[CH:14]=[C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]1=[O:21].C(=O)([O-])[O-].[K+].[K+]>N1CCCCC1>[N:5]1([CH2:2][CH2:3][CH2:4][N:5]2[CH:14]=[C:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:6]2=[O:21])[CH2:14][CH2:13][CH2:12][CH2:7][CH2:6]1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 128129652-(3-chloropropyl)-4-phenyl-1(2H)-isoquinolone

Product 1

HCID 131747412-(3-piperidinopropyl)-4-phenyl-1(2H)-isoquinoloneYield 180%

Reagents, catalysts & solvents 1

HCID 8082PiperidineSolvent

Procedure

Then, 14.9 g of 2-(3-chloropropyl)-4-phenyl-1(2H)-isoquinolone, 7 g of anhydrous potassium carbonate and 40 ml of piperidine were mixed and heated at reflux for 5 hours. Thereafter, any excess of piperidine was distilled off and the residue was dissolved in dichloromethane. The solution was washed with water, dried and the solvent was distilled off. The resulting crystals were recrystallized from a mixture of diethyl ether and petroleum ether to obtain 15.6 g of 2-(3-piperidinopropyl)-4-phenyl-1(2H)-isoquinolone having a melting point of 117.5° C. as colorless prisms.

Workup

  1. temperatureheated
  2. temperatureat reflux for 5 hours
  3. distillationThereafter, any excess of piperidine was distilled off
  4. dissolutionthe residue was dissolved in dichloromethane
  5. washThe solution was washed with water
  6. customdried
  7. distillationthe solvent was distilled off
  8. customThe resulting crystals were recrystallized from a mixture of diethyl ether and petroleum ether

Sources & evidence

ORD record
ord-ca40588b2ee04409a36c6936f2d90ad6
Source dataset
uspto-grants-1983_07
Patent number
US04393210

Reaction notes

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