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

HRID 1645916Notes

Reaction equation

HRID 1645916 reaction equation
Cl[CH2:2][CH2:3][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>[N:17]1([CH2:2][CH2:3][CH2:4][O:5][C:6]2[CH:15]=[CH:14][CH:13]=[C:12]3[C:7]=2[CH2:8][CH2:9][NH:10][C:11]3=[O:16])[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1

Participants

4

Reactant 2

HCID 8082PiperidineHCID 110755405-(3-Chloropropoxy)-3,4-dihydroisoquinolin-1(2H)-one

Product 1

HCID 183695103,4-Dihydro-5-[3-(1-piperidinyl)propoxy]-1(2H)-isoquinolinoneYield 61%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 0.6 g (2.5 mmol) of 5-(3-chloropropoxy)-3,4-dihydro-1(2H)-isoquinolinone and 0.6 ml (10 mmol) of piperidine in 30 ml of ethanol was refluxed for 40 hours. The mixture was concentrated, dissolved in chloroform and washed with saturated sodium bicarbonate. The organic layer was dried and concentrated. The solid was recrystallized from water to provide 0.44 g (61%) of the desired product; mp 112°-114°.

Workup

  1. temperaturewas refluxed for 40 hours
  2. concentrationThe mixture was concentrated
  3. dissolutiondissolved in chloroform
  4. washwashed with saturated sodium bicarbonate
  5. customThe organic layer was dried
  6. concentrationconcentrated
  7. customThe solid was recrystallized from water

Sources & evidence

ORD record
ord-f83c02719f95441f9576a7189413742b
Source dataset
uspto-grants-1993_01
Patent number
US05177075

Reaction notes

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