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Hydrochloric Acid → 4-{3-[4-(3-Hydroxypropyl)-1-piperidinyl]propoxy}benzonitrile monohydrate

HRID 43275
Notes
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Reaction equation

HRID 43275 reaction equation
CS(O[CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]#[N:17])=[CH:12][CH:11]=1)(=O)=[O:3].[I-].[K+].C(=O)(O)[O-].[Na+].Cl.[NH:26]1[CH2:31][CH2:30][CH:29]([CH2:32][CH2:33][CH2:34][OH:35])[CH2:28][CH2:27]1.Cl>CN(C)C=O.C1(C)C=CC=CC=1.O>[OH2:3].[OH:35][CH2:34][CH2:33][CH2:32][CH:29]1[CH2:30][CH2:31][N:26]([CH2:6][CH2:7][CH2:8][O:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]#[N:17])=[CH:12][CH:11]=2)[CH2:27][CH2:28]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 4875Potassium IodideHCID 516892Sodium BicarbonateHCID 184257203-(Piperidin-4-yl)propan-1-ol hydrochlorideHCID 860892793-(4-Cyanophenoxy)propyl methanesulfonate

Product 1

HCID 684343824-{3-[4-(3-Hydroxypropyl)-1-piperidinyl]propoxy}benzonitrile monohydrate
Yield 83.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

Into a solution of 50.0 g of 3-(4-cyanophenoxy)propyl methanesulfonate in 250 mL of N,N-dimethylformamide, 32.5 g of potassium iodide, 32.9 g of sodium bicarbonate and 37.0 g of 3-(4-piperidinyl)-1-propanol hydrochloride were added at room temperature, which was then stirred at 70° C. for 7 hours. To the reaction mixture, after being cooled down to room temperature, 250 mL of water and 150 mL of toluene were added, and then hydrochloric acid was added to adjust the pH to 1.0. The aqueous layer was separated, adjusted to pH 10.0 with a 20% sodium hydroxide aqueous solution, and stirred at room temperature for 15 min and under cooling on ice for 30 min. The solid matter was collected by filtration and washed twice with 50 mL of water and twice with 50 mL of toluene to obtain 52.3 g of 4-{3-[4-(3-hydroxypropyl)-1-piperidinyl]propoxy}benzonitrile monohydrate as a white solid.

Workup

  1. temperatureTo the reaction mixture, after being cooled down to room temperature
  2. customThe aqueous layer was separated
  3. stirringstirred at room temperature for 15 min
  4. temperatureunder cooling on ice for 30 min
  5. filtrationThe solid matter was collected by filtration
  6. washwashed twice with 50 mL of water and twice with 50 mL of toluene

Sources & evidence

ORD record
ord-236e301dba894c7bb118600cfe5dbadb
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