Hydrochloric Acid → 1-(4-Hydroxypiperidin-1-yl)cyclohexane-1-carbonitrile

HRID 466260

Reaction equation

HRID 466260 reaction equation
O[N:2]1[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.Cl.[C:9]1(=O)[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1.[C-:16]#[N:17].[K+].[OH2:19]>>[C:16]([C:9]1([N:2]2[CH2:7][CH2:6][CH:5]([OH:19])[CH2:4][CH2:3]2)[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1)#[N:17]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 962Water2×HCID 7967CyclohexanoneHCID 9032Potassium CyanideHCID 209351-Hydroxypiperidine2×

Product 1

HCID 100589041-(4-Hydroxypiperidin-1-yl)cyclohexane-1-carbonitrile

Conditions

Temperature
0 °C

Procedure

4 hydroxypiperidine (Aldrich Chemical Co., Inc., supra) (5q) was dissolved in distilled water (14 mL), cooled to 0° C. and the pH was adjusted to between 4 and 5 by addition of concentrated hydrochloric acid and 4 hydroxypiperidine. After warming to room temperature, 5.2 mL cyclohexanone and 3.3 g potassium cyanide in water (9 mL) were added sequentially. After 18 hours of stirring at room temperature, the solid was filtered. The solid was dissolved in 100 mL methylene chloride, dried over Na2SO4, filtered and the solvent was removed in vacuo to yield pure 1 (1 cyanocyclohexyl) 4 hydroxypiperidine.

Workup

  1. temperatureAfter warming to room temperature
  2. filtrationthe solid was filtered
  3. dissolutionThe solid was dissolved in 100 mL methylene chloride
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-a4eb416b22e64863aba5506a62cab93e
Source dataset
uspto-grants-1992_10
Patent number
US05155212

Linked notes

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