Dimethylformamide → HCID 59263018, compound

HRID 644130Notes

Reaction equation

HRID 644130 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][OH:34]>O.C(Cl)(Cl)Cl>[OH:34][CH2:33][CH2:32][CH2:31][N:6]1[CH2:11][CH2:10][CH:9]([CH2:12][CH2:13][CH2:14][O:15][C:16]2[CH:17]=[CH:18][C:19]([C:20]#[N:21])=[CH:22][CH:23]=2)[CH2:8][CH2:7]1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 123083-Bromo-1-propanol2×HCID 592630194-[3-(4-Piperidinyl)propoxy]benzonitrile

Product 1

HCID 59263018HCID 59263018, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

To an N,N-dimethylformamide (70 mL) solution of 9.81 g of 4-[3-(4-piperidinyl)propoxy]benzonitrile were added 8.02 g of potassium carbonate and 2.62 mL of 3-bromo-1-propanol at room temperature, which was then stirred at the same temperature for 2 hours and 15 minutes. Thereto was added 2.62 mL of 3-bromo-1-propanol, which was then stirred at the same temperature for 1 hour and 45 minutes. Chloroform and water were added to the reaction mixture. The organic layer was separated, washed sequentially with a 1 mol/L sodium hydroxide aqueous solution and a saturated sodium chloride aqueous solution, and then dried with anhydrous magnesium sulfate, followed by distilling off the solvent under reduced pressure. The resultant residue was purified using silica gel column chromatography (eluent; chloroform:methanol=4:1) to provide 4.28 g of 4-{3-[1-(3-hydroxypropyl)-4-piperidinyl]propoxy}benzonitrile as white solid form.

Workup

  1. stirringwas then stirred at the same temperature for 1 hour and 45 minutes
  2. customThe organic layer was separated
  3. washwashed sequentially with a 1 mol/L sodium hydroxide aqueous solution
  4. dry with materiala saturated sodium chloride aqueous solution, and then dried with anhydrous magnesium sulfate
  5. distillationby distilling off the solvent under reduced pressure
  6. customThe resultant residue was purified

Sources & evidence

ORD record
ord-14044674602b47c1b52e0dc261b66009
Source dataset
uspto-grants-2010_04
Patent number
US07700623B2

Reaction notes

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