Acetic Acid → 1-Benzyl-4-(4-(pyridin-4-yl)piperazin-1-yl)piperidine-4-carbonitrile

HRID 46002Notes

Reaction equation

HRID 46002 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([N:7]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)=[CH:3][CH:2]=1.[CH2:13]([N:20]1[CH2:25][CH2:24][CH2:23][CH2:22][C:21]1=O)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[C-:27]#[N:28].[K+].CC(O)=O>CO.O>[CH2:13]([N:20]1[CH2:25][CH2:24][C:23]([N:10]2[CH2:9][CH2:8][N:7]([C:4]3[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=3)[CH2:12][CH2:11]2)([C:27]#[N:28])[CH2:22][CH2:21]1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 9032Potassium CyanideHCID 705171-(4-Pyridyl)piperazineHCID 51700761-Benzyl-2-piperidone

Product 1

HCID 686295031-Benzyl-4-(4-(pyridin-4-yl)piperazin-1-yl)piperidine-4-carbonitrileYield 47%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution containing 1-(pyridin-4-yl)piperazine (58.34 mmol, 1 equiv.), N-benzyl-piperidinone (1 equiv.), KCN (1.1 equiv.), AcOH (3.3 ml) and water (1.3 ml) in methanol was stirred at room temperature for 16 h. The reaction mixture was quenched with NH4OH solution (400 ml) and filtered. The solid precipitate was thoroughly washed with water, dried under vacuum and taken through to the next reaction without further purification. Yield: 47%.

Workup

  1. customThe reaction mixture was quenched with NH4OH solution (400 ml)
  2. filtrationfiltered
  3. washThe solid precipitate was thoroughly washed with water
  4. customdried under vacuum
  5. customtaken through to the next reaction without further purification

Sources & evidence

ORD record
ord-4fa8de6172fc453393300fd777b7a17a
Source dataset
uspto-grants-2013_09
Patent number
US08541573B2

Reaction notes

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