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

HRID 1588220Notes

Reaction equation

HRID 1588220 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) (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 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-4c3ef08d1b6b472996e7165b75d14bd6
Source dataset
uspto-grants-1993_06
Patent number
US05221629

Reaction notes

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