Chloroacetonitrile → 2-(4-(Isoquinolin-1-yl)piperazin-1-yl)acetonitrile

HRID 600465Notes

Reaction equation

HRID 600465 reaction equation
[N:1]1([C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH:10]=[CH:9][N:8]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[CH3:17][CH2:18][N:19](CC)CC.ClCC#N>C1COCC1>[C:7]1([N:1]2[CH2:2][CH2:3][N:4]([CH2:17][C:18]#[N:19])[CH2:5][CH2:6]2)[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9][N:8]=1

Participants

5

Reactant 3

HCID 7856ChloroacetonitrileHCID 8471TriethylamineHCID 158874361-(Piperazin-1-yl)isoquinoline

Product 1

HCID 597292672-(4-(Isoquinolin-1-yl)piperazin-1-yl)acetonitrileYield 35%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-(piperazin-1-yl)isoquinoline (459 mg, 2.15 mmol) in THF (15 mL) was added NEt3 (3.6 mL, 27 mmol) and chloroacetonitrile (1.8 mL, 28 mmol) and the reaction was stirred 3 h. The reaction mixture was filtered, concentrated and the residue purified by silica gel chromatography (Biotage 25-short, 25% EtOAc/hexanes to 100% EtOAc/hex) to yield 38 (188 mg, 0.75 mmol, 35%) as a white solid. LC/MS: (ES+) m/z (M+H)+=253; HPLC Rt=1.23 min., column Q, conditions B.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated
  3. customthe residue purified by silica gel chromatography (Biotage 25-short, 25% EtOAc/hexanes to 100% EtOAc/hex)

Sources & evidence

ORD record
ord-db06c371b96943ff923e7e3210718657
Source dataset
uspto-grants-2011_03
Patent number
US07902204B2

Reaction notes

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