Water → 1-(2-Cyano-4-nitrophenyl)-4-piperidinyl benzoate

HRID 1744531Notes

Reaction equation

HRID 1744531 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([N:12]2[CH2:17][CH2:16][CH:15]([OH:18])[CH2:14][CH2:13]2)=[C:8]([CH:11]=1)[C:9]#[N:10])([O-:3])=[O:2].C1(C)C=CC=CC=1.[C:26](Cl)(=[O:33])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.O>N1C=CC=CC=1>[C:26]([O:18][CH:15]1[CH2:14][CH2:13][N:12]([C:7]2[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:11][C:8]=2[C:9]#[N:10])[CH2:17][CH2:16]1)(=[O:33])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1140TolueneHCID 7412Benzoyl chlorideHCID 172213732-(4-Hydroxypiperidin-1-yl)-5-nitrobenzonitrile

Product 1

HCID 222280761-(2-Cyano-4-nitrophenyl)-4-piperidinyl benzoateYield 113.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

5-Nitro-2-(4-hydroxypiperidin-1-yl)benzonitrile (20 g) was dissolved in pyridine (100 ml). To the solution was added dropwise toluene solution (50 ml) containing benzoyl chloride (12.8 g) under ice-cooling, and the mixture was stirred at room temperature for 3 h. The reaction mixture was poured into water. The obtained crystals were recrystallized from a mixed solvent of ethyl acetate-n-hexane to give 1-(2-cyano-4-nitrophenyl)-4-piperidinyl benzoate (32.3 g), melting point: 143–145° C.

Workup

  1. temperaturecooling
  2. customThe obtained crystals were recrystallized from a mixed solvent of ethyl acetate-n-hexane

Sources & evidence

ORD record
ord-8717a1cdf764420aafe2b3ed59f4b77d
Source dataset
uspto-grants-2006_03
Patent number
US07015218B1

Reaction notes

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