Nitrogen → 2-benzyl-5-piperazin-1-yl-3,4-dihydro-2H-isoquinolin-1-one

HRID 459838Notes

Reaction equation

HRID 459838 reaction equation
[CH2:1]([N:8]1[CH:17]=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][C:14]=2[N:18]2[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]2)[C:9]1=[O:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N#N.[H][H]>CCO.[Pd]>[CH2:1]([N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][C:14]=2[N:18]2[CH2:19][CH2:20][NH:21][CH2:22][CH2:23]2)[C:9]1=[O:24])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 947NitrogenHCID 184445292-benzyl-5-piperazin-1-yl-2H-isoquinolin-1-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 103140052-benzyl-5-piperazin-1-yl-3,4-dihydro-2H-isoquinolin-1-oneYield 15.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

2-Benzyl-5-piperazin-1-yl-2H-isoquinolin-1-one (0.05 g, 0.16 mmol) from step 5 was added to a small (100 mL) Parr bottle, dissolved in 10 mL of EtOH, and a catalytic amount (25 mg) of palladium (10%) on charcoal was added (under N2 atmosphere). The vessel was then exposed to 60 psig hydrogen for 24 hours. Preparative HPLC gave the desired product, 2-benzyl-5-piperazin-1-yl-3,4-dihydro-2H-isoquinolin-1-one (8 mg, 0.025 mmol); M+H=322.

Sources & evidence

ORD record
ord-5ce567a4e8394a8b83804f15b58a4f3f
Source dataset
uspto-grants-2007_03
Patent number
US07196088B2

Reaction notes

Loading…