Water → 1-[4-Benzyl-(1-piperazinyl)]isoquinoline

HRID 365293Notes

Reaction equation

HRID 365293 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][N:3]=1.[CH2:12]([N:19]1[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(N(CC)C(C)C)(C)C.O>CN(C=O)C>[CH2:12]([N:19]1[CH2:24][CH2:23][N:22]([C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[CH:5]=[CH:4][N:3]=2)[CH2:21][CH2:20]1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 962WaterHCID 759941-BenzylpiperazineHCID 81531DiisopropylethylamineHCID 140539Isoquinoline, 1-chloro-

Product 1

HCID 224680261-[4-Benzyl-(1-piperazinyl)]isoquinolineYield 40.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 1-chloroisoquinoline (1.64 g 10 mmol) in dry DMF (5 ml) was added to a stirred solution of 1-benzylpiperazine (1.85 g, 10.5 mmol) and N,N-diisopropylethylamine (2 ml, 1.5 g, 11.5 mmol) in dry DMF (5 ml) under Ar at room temperature. The solution was stirred at room temperature for 17 h. The yellow solution was heated at 110° C. for 7 h, treated with water (100 ml) and extracted with ether (2×50 ml). The extracts were dried (Na2SO4) and concentrated in vacuo. The residue was chromatographed (SiO2 ; ethyl acetate) to give the product (1.233 g).

Workup

  1. temperatureThe yellow solution was heated at 110° C. for 7 h
  2. extractionextracted with ether (2×50 ml)
  3. dry with materialThe extracts were dried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customThe residue was chromatographed (SiO2 ; ethyl acetate)

Sources & evidence

ORD record
ord-83cf8d208096407f9854c5332bf0ae09
Source dataset
uspto-grants-2000_10
Patent number
US06127357

Reaction notes

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