Chloroacetonitrile → HCID 178511314, compound

HRID 2229703Notes

Reaction equation

HRID 2229703 reaction equation
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH:11]3[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]3)=[N:7][NH:8]2)=[CH:4][CH:3]=1.C([O-])(O)=O.[Na+].Cl[CH2:23][C:24]#[N:25].C(Cl)Cl.CCOC(C)=O>C(#N)C>[F:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH:11]3[CH2:16][CH2:15][N:14]([CH2:23][C:24]#[N:25])[CH2:13][CH2:12]3)=[N:7][NH:8]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 7856ChloroacetonitrileHCID 516892Sodium BicarbonateHCID 21226138Dichloromethane ethylacetateHCID 178505426HCID 178505426, compound

Product 1

HCID 178511314HCID 178511314, compoundYield 89.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred suspension of 4-(6-fluoro-1H-indazol-3yl)piperidine (4.95 g, 22.6 mmol) and NaHCO3 (2.1 g, 24.9 mmol) in dry acetonitrile (110 ml) was added chloroacetonitrile (1.6 ml, 24.9 mmol) at room temperature, under nitrogen. The suspension was warmed to reflux for 22.5 hours, cooled to room temperature, and subsequently filtered. The remaining solids were washed with DCM and the combined filtrates were concentrated. The resulting brown oil was dissolved into EtOAc and washed with water. The organic phase was dried (MgSO4, filtered and concentrated to give a brown solid which was re-dissolved into DCM/EtOAc and flushed through alumina with DCM. The eluent was concentrated to give 5.2 g of the desired product as a solid, m.p. 149-151° C.

Workup

  1. temperatureThe suspension was warmed
  2. temperatureto reflux for 22.5 hours
  3. filtrationsubsequently filtered
  4. washThe remaining solids were washed with DCM
  5. concentrationthe combined filtrates were concentrated
  6. dissolutionThe resulting brown oil was dissolved into EtOAc
  7. washwashed with water
  8. dry with materialThe organic phase was dried (MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customto give a brown solid which
  12. customflushed through alumina with DCM
  13. concentrationThe eluent was concentrated

Sources & evidence

ORD record
ord-9eaf28ee9dde4ca39e8ffba1424ff21a
Source dataset
uspto-grants-2002_07
Patent number
US06420390B1

Reaction notes

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