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

HRID 45994

Reaction equation

HRID 45994 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11](=O)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(=O)C.[CH:19]1([N:22]2[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]2)[CH2:21][CH2:20]1.[C-:28]#[N:29].[K+]>CO.O>[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([N:25]2[CH2:26][CH2:27][N:22]([CH:19]3[CH2:21][CH2:20]3)[CH2:23][CH2:24]2)([C:28]#[N:29])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 9032Potassium CyanideHCID 192201-Benzyl-4-piperidoneHCID 47420041-Cyclopropylpiperazine

Product 1

HCID 579895831-Benzyl-4-(4-cyclopropylpiperazin-1-yl)piperidine-4-carbonitrileYield 53%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 1-benzylpiperidin-4-one (26.42 mmol, 1.0 equiv.) and acetic acid (26.42 mmol, 1.0 equiv.) in methanol (10 ml) were added water (600 ml), N-cyclopropyl piperazine (29.06 mmol, 1.1 equiv.), and potassium cyanide (26.42 mmol, 1.0 equiv.). The resulting reaction mixture was stirred at room temperature for 1 h by which time a solid had separated. The solid was collected by filtration, washed with water and dried to obtain the desired product which was used in the next step without further purification. Yield: 53%.

Workup

  1. customThe resulting reaction mixture
  2. customhad separated
  3. filtrationThe solid was collected by filtration
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-b0461ed294b34c63a0d1e82e53f87772
Source dataset
uspto-grants-2013_09
Patent number
US08541573B2

Linked notes

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