Piperidine → 3,4-Dihydro-5-[2-hydroxy-3-(1-piperidinyl)propoxy]-1(2H)-isoquinolinone

HRID 1645898Notes

Reaction equation

HRID 1645898 reaction equation
[O:1]1[CH2:3][CH:2]1[CH2:4][O:5][C:6]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:7]=1[CH2:8][CH2:9][NH:10][C:11]2=[O:16].[NH:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1>C(O)C>[OH:1][CH:2]([CH2:3][N:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1)[CH2:4][O:5][C:6]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:7]=1[CH2:8][CH2:9][NH:10][C:11]2=[O:16]

Participants

4

Reactant 2

HCID 8082PiperidineHCID 232893633,4-Dihydro-5-(2-oxiranylmethoxy)-1(2H)-isoquinolinone

Product 1

HCID 183695033,4-Dihydro-5-[2-hydroxy-3-(1-piperidinyl)propoxy]-1(2H)-isoquinolinoneYield 67%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3.0 g (13.7 mmol) of 3,4-Dihydro-5-(2-oxiranylmethoxy)-1(2H)-isoquinolinone, 1.4 g of piperidine (13.7 mmol), and 30 ml of ethanol was heated at reflux for five hours. The mixture was concentrated and the residue was recrystallized from ethanol/acetone (2/3) to give 2.78 g (67%) of the desired product; mp 162°-164°.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for five hours
  3. concentrationThe mixture was concentrated
  4. customthe residue was recrystallized from ethanol/acetone (2/3)

Sources & evidence

ORD record
ord-52b327f891974503a5245f5714132066
Source dataset
uspto-grants-1993_01
Patent number
US05177075

Reaction notes

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