Dimethylformamide → 4-(3-{4-[3-(4-Cyanophenoxy)propyl]-1-piperidinyl}propoxy)benzonitrile

HRID 881027Notes

Reaction equation

HRID 881027 reaction equation
CN(C)C=O.[NH:6]1[CH2:11][CH2:10][CH:9]([CH2:12][CH2:13][CH2:14][O:15][C:16]2[CH:23]=[CH:22][C:19]([C:20]#[N:21])=[CH:18][CH:17]=2)[CH2:8][CH2:7]1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:31][CH2:32][CH2:33][O:34][C:35]1[CH:42]=[CH:41][C:38]([C:39]#[N:40])=[CH:37][CH:36]=1>O.C1(C)C=CC=CC=1>[C:20]([C:19]1[CH:18]=[CH:17][C:16]([O:15][CH2:14][CH2:13][CH2:12][CH:9]2[CH2:10][CH2:11][N:6]([CH2:31][CH2:32][CH2:33][O:34][C:35]3[CH:42]=[CH:41][C:38]([C:39]#[N:40])=[CH:37][CH:36]=3)[CH2:7][CH2:8]2)=[CH:23][CH:22]=1)#[N:21]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 10879224HCID 10879224, compoundHCID 592630194-[3-(4-Piperidinyl)propoxy]benzonitrile

Product 1

HCID 162222054-(3-{4-[3-(4-Cyanophenoxy)propyl]-1-piperidinyl}propoxy)benzonitrileYield 83.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

To an N,N-dimethylformamide (150 mL) solution of 10.2 g of 4-[3-(4-piperidinyl)propoxy]benzonitrile were sequentially added 11.2 g of potassium carbonate and 9.72 g of 4-(3-bromopropoxy)benzonitrile at room temperature, which was then stirred at the same temperature for 18 hours. Toluene and water were added to the reaction mixture. The precipitate was collected by filtration to provide 13.7 g of 4-(3-{4-[3-(4-cyanophenoxy)propyl]-1-piperidinyl}propoxy)benzonitrile as white solid form.

Workup

  1. customat room temperature
  2. filtrationThe precipitate was collected by filtration

Sources & evidence

ORD record
ord-8dcd3864fe3e487ab4ccd0af48b921e6
Source dataset
uspto-grants-2015_03
Patent number
US08993603B2

Reaction notes

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