Bis(2-chloroethyl)amine hydrochloride → 2-benzyl-5-piperazin-1-yl-2H-isoquinolin-1-one

HRID 459837Notes

Reaction equation

HRID 459837 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][N:6]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:7]2=[O:12].Cl.Cl[CH2:22][CH2:23][NH:24][CH2:25][CH2:26]Cl>>[CH2:13]([N:6]1[CH:5]=[CH:4][C:3]2[C:8](=[CH:9][CH:10]=[CH:11][C:2]=2[N:1]2[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]2)[C:7]1=[O:12])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

3

Reactant 2

HCID 522769Bis(2-chloroethyl)amine hydrochlorideHCID 184445335-amino-2-benzylisoquinolin-1(2H)-one

Product 1

HCID 184445292-benzyl-5-piperazin-1-yl-2H-isoquinolin-1-one

Procedure

5-Amino-2-benzyl-2H-isoquinolin-1-one (0.687 g, 2.75 mmol)) from step 4 was combined with excess bis-(2-chloroethyl)-amine hydrochloride and heated to a melt for 5 minutes. TLC analysis showed one major product and several minor side products. The reaction mixture was chromatographed over silica gel (CH2Cl2/MeOH, 95:5) to afford 2-benzyl-5-piperazin-1-yl-2H-isoquinolin-1-one (0.103 mg, 0.32 mmol); M+H=320.

Workup

  1. temperatureheated to a melt for 5 minutes
  2. customThe reaction mixture was chromatographed over silica gel (CH2Cl2/MeOH, 95:5)

Sources & evidence

ORD record
ord-d295d00dbad54b4d9942507b8f358343
Source dataset
uspto-grants-2007_03
Patent number
US07196088B2

Reaction notes

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