Chloroacetonitrile → [4-(1H-Indazol-3-yl)1-piperazinyl]acetonitrile

HRID 1601300Notes

Reaction equation

HRID 1601300 reaction equation
[N:1]1([C:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[NH:9][N:8]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.C([O-])(O)=O.[Na+].Cl[CH2:22][C:23]#[N:24]>C(#N)C>[NH:9]1[C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:7]([N:1]2[CH2:6][CH2:5][N:4]([CH2:22][C:23]#[N:24])[CH2:3][CH2:2]2)=[N:8]1

Participants

5

Reactant 3

HCID 7856ChloroacetonitrileHCID 516892Sodium BicarbonateHCID 148234453-(Piperazin-1-YL)-1H-indazole

Product 1

HCID 18467291[4-(1H-Indazol-3-yl)1-piperazinyl]acetonitrileYield 55.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred suspension of 3-piperazin-1-yl-1H-indazole (6.0 g, 29.7 mmol) and NaHCO3 (2.7 g, 32.7 mmol) in dry acetonitrile (125 ml) was added chloroacetonitrile (2.1 ml, 31.2 mmol) at room temperature, under nitrogen. The suspension was warmed to reflux for 17.5 hours, cooled to room temperature, and subsequently filtered. The remaining solids were washed with dichloromethane and the combined filtrates were concentrated. The resulting brown oil was purified via flash column chromatography (silica gel, 0-50% EtOAc/DCM) to give 4.0 g of product as an off-white solid, m.p. 121-123° C.

Workup

  1. temperatureThe suspension was warmed
  2. temperatureto reflux for 17.5 hours
  3. filtrationsubsequently filtered
  4. washThe remaining solids were washed with dichloromethane
  5. concentrationthe combined filtrates were concentrated
  6. customThe resulting brown oil was purified via flash column chromatography (silica gel, 0-50% EtOAc/DCM)

Sources & evidence

ORD record
ord-e1bb038fe2704658a2ed2dd34e62c8fa
Source dataset
uspto-grants-1999_11
Patent number
US05977113

Reaction notes

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