Hydrochloric Acid → 4-Hydroxy-1-methylpiperidine-4-carbonitrile

HRID 1458762Notes

Reaction equation

HRID 1458762 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][C:5](=[O:8])[CH2:4][CH2:3]1.Cl.[C-:10]#[N:11].[K+]>O>[OH:8][C:5]1([C:10]#[N:11])[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 9032Potassium CyanideHCID 740491-Methyl-4-piperidone

Product 1

HCID 2840534-Hydroxy-1-methylpiperidine-4-carbonitrileYield 67%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
10 °C

Procedure

To freshly distilled 1-methylpiperidin-4-one (81.72 g, 0.72 mole) in water (200 cc), were added about 100 cc HCl 37% to pH 3. The reaction mixture was cooled in an ice bath and potassium cyanide (49 g, 0.75 mole) in water (200 cc) was added at an adequate rate in order to maintain an internal temperature of about 10° C. The reaction was stirred two hours more after the addition and then filtered. After washing with water and drying, the product, 4-hydroxy-4-cyano-1-methylpiperidine, was obtained in 67% yield as a white powder (67 g, 0.48 mole, mp. 135° C.),

Workup

  1. temperatureThe reaction mixture was cooled in an ice bath
  2. additionmore after the addition
  3. filtrationfiltered
  4. washAfter washing with water
  5. customdrying

Sources & evidence

ORD record
ord-45007ed711c047f08a7c8093ecf699a1
Source dataset
uspto-grants-1998_12
Patent number
US05852029

Reaction notes

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