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

HRID 1654442Notes

Reaction equation

HRID 1654442 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][NH: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+]>O>[C:16]([C:9]1([N:5]2[CH2:6][CH2:7][CH:2]([OH:1])[CH2:3][CH2:4]2)[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1)#[N:17]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7967CyclohexanoneHCID 9032Potassium CyanideHCID 79341Piperidin-4-ol2×

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

4-hydroxypiperidine (Aldrich Chemical Co., Inc., supra) (5 g) 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-e9eb45a7ba054cfdad2ba32fbf3cd446
Source dataset
uspto-grants-1995_04
Patent number
US05407834

Reaction notes

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