Hydrochloric Acid → HCID 68434383, compound

HRID 644126Notes

Reaction equation

HRID 644126 reaction equation
CS([O-])(=O)=O.[I-].[K+].[C:8](=[O:11])(O)[O-].[Na+].Cl.[NH:14]1[CH2:19][CH2:18][CH:17]([CH2:20][CH2:21][CH2:22][OH:23])[CH2:16][CH2:15]1.Cl.C[N:26]([CH3:29])C=O>C1(C)C=CC=CC=1.O>[OH:23][CH2:22][CH2:21][CH2:20][CH:17]1[CH2:18][CH2:19][N:14]([CH2:20][CH2:21][CH2:22][O:11][C:8]2[CH:19]=[CH:18][C:17]([C:29]#[N:26])=[CH:16][CH:15]=2)[CH2:15][CH2:16]1

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 4875Potassium IodideHCID 6228DimethylformamideHCID 85257MethanesulfonateHCID 516892Sodium BicarbonateHCID 184257203-(Piperidin-4-yl)propan-1-ol hydrochloride

Product 1

HCID 68434383HCID 68434383, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
70 °C

Procedure

To an N,N-dimethylformamide (250 mL) solution of 50.0 g of 3-(4-cyanophenoxy)propyl=methanesulfonate were added 32.5 g of potassium iodide, 32.9 g of sodium bicarbonate, and 37.0 g of 3-(4-piperidinyl)-1-propanol hydrochloride at room temperature, which was then stirred at 70° C. for 6 hours and 50 minutes. The reaction mixture was cooled down to room temperature, to which water and toluene were then added, followed by adjustment to pH 1.0 using hydrochloric acid. The aqueous layer was separated, adjusted to pH 10.0 using a 20% sodium hydroxide aqueous solution, and stirred at room temperature for 15 minutes and then under cooling with ice for 30 minutes. The precipitate was collected by filtration and washed with water and toluene to provide 52.3 g of 4-{3-[4-(3-hydroxypropyl)-1-piperidinyl]propoxy}benzonitrile as white solid form.

Workup

  1. additionwere then added
  2. customThe aqueous layer was separated
  3. stirringstirred at room temperature for 15 minutes
  4. temperatureunder cooling with ice for 30 minutes
  5. filtrationThe precipitate was collected by filtration
  6. washwashed with water and toluene

Sources & evidence

ORD record
ord-b027ad3d691d4f0d98c8857cedf8e7fe
Source dataset
uspto-grants-2010_04
Patent number
US07700623B2

Reaction notes

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