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

HRID 43276
Notes
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Reaction equation

HRID 43276 reaction equation
CS([O:5][CH2:6][CH2:7][CH2:8][CH:9]1[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][O:18][C:19]2[CH:24]=[CH:23][C:22]([C:25]#[N:26])=[CH:21][CH:20]=2)[CH2:11][CH2:10]1)(=O)=O.C(=O)([O-])[O-].[K+].[K+].[C:33]([C:35]1[CH:40]=[CH:39][C:38](O)=[CH:37][CH:36]=1)#[N:34].O>CS(C)=O>[C:33]([C:35]1[CH:40]=[CH:39][C:38]([O:5][CH2:6][CH2:7][CH2:8][CH:9]2[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][O:18][C:19]3[CH:24]=[CH:23][C:22]([C:25]#[N:26])=[CH:21][CH:20]=3)[CH2:11][CH2:10]2)=[CH:37][CH:36]=1)#[N:34]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 130194-CyanophenolHCID 866383033-{1-[3-(4-Cyanophenoxy)propyl]-4-piperidinyl}propyl methanesulfonate

Product 1

HCID 162222054-(3-{4-[3-(4-Cyanophenoxy)propyl]-1-piperidinyl}propoxy)benzonitrileYield 92.3%

Reagents, catalysts & solvents 1

HCID 679
Dimethyl Sulfoxide
Solvent

Conditions

Temperature
60 °C

Procedure

Into a solution of 91.9 g of 3-{1-[3-(4-cyanophenoxy)propyl]-4-piperidinyl}propyl methanesulfonate in 460 mL of dimethylsulfoxide, 66.9 g of potassium carbonate and 28.8 g of 4-cyanophenol were added at room temperature, and the solution was stirred at 60° C. for 2 hours. To the reaction mixture, after being cooled down to room temperature, 640 mL of water was dropped over 20 min, and then the mixture was stirred at room temperature for 35 min, and under water cooling for 30 min. The solid matter was collected by filtration, and washed twice with 180 mL of water and then 360 mL of 2-propanol to obtain 90.0 g of 4-(3-{4-[3-(4-cyanophenoxy)propyl]-1-piperidinyl}propoxy)benzonitrile as a white solid.

Workup

  1. temperatureTo the reaction mixture, after being cooled down to room temperature
  2. stirringthe mixture was stirred at room temperature for 35 min
  3. waitunder water cooling for 30 min
  4. filtrationThe solid matter was collected by filtration
  5. washwashed twice with 180 mL of water

Sources & evidence

ORD record
ord-0b765a27ecc84227ad29661102c5ddc6
Source dataset
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08536343B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes