Water → HCID 14986271, compound

HRID 2248765Notes

Reaction equation

HRID 2248765 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([N:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)[C:3]=1[C:4]#[N:5].N1C=CC=CC=1.[C:22]([O:25][CH2:26][C:27](Cl)=[O:28])(=[O:24])[CH3:23].O>C(Cl)Cl>[C:22]([O:25][CH2:26][C:27]([NH:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([N:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)[C:3]=1[C:4]#[N:5])=[O:28])(=[O:24])[CH3:23]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 26297Acetoxyacetyl chlorideHCID 127157252-Amino-6-(1-piperidinyl)benzonitrile

Product 1

HCID 14986271HCID 14986271, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-amino-6-piperidinobenzonitrile (8.8 g) in methylene chloride (100 ml) is added pyridine (3.3 ml), and thereto is added dropwise acetoxyacetyl chloride (4.3 ml) which is cooled in an ice bath. The mixture is stirred at room temperature for 1 hour, and thereafter, water is added thereto, and the mixture is extracted with methylene chloride. The organic layer is dried over anhydrous sodium sulfate, and the solvent is distilled off under reduced pressure. The resulting crude crystals are recrystallized from ethyl acetate-hexane to give the title compound (3.2 g) having the following physical properties.

Workup

  1. temperatureis cooled in an ice bath
  2. extractionthe mixture is extracted with methylene chloride
  3. dry with materialThe organic layer is dried over anhydrous sodium sulfate
  4. distillationthe solvent is distilled off under reduced pressure
  5. customThe resulting crude crystals are recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-21b7d1c0ecdc4db28f90739573b6b140
Source dataset
uspto-grants-1991_08
Patent number
US05041462

Reaction notes

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