Potassium Cyanide → 4-(3-Hydroxypiperidino)-tetrahydro-4h-thiopyran-4-carbonitrile

HRID 1251369Notes

Reaction equation

HRID 1251369 reaction equation
Cl.[OH:2][CH:3]1[CH2:8][CH2:7][CH2:6][NH:5][CH2:4]1.[C-:9]#[N:10].[K+].[S:12]1[CH2:17][CH2:16][C:15](=O)[CH2:14][CH2:13]1>O>[OH:2][CH:3]1[CH2:8][CH2:7][CH2:6][N:5]([C:15]2([C:9]#[N:10])[CH2:16][CH2:17][S:12][CH2:13][CH2:14]2)[CH2:4]1

Participants

5

Reactant 3

HCID 9032Potassium CyanideHCID 66173Tetrahydrothiopyran-4-oneHCID 2723962Piperidine-3-ol hydrochloride

Product 1

HCID 183239584-(3-Hydroxypiperidino)-tetrahydro-4h-thiopyran-4-carbonitrile

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3-hydroxy-piperidine hydrochloride (6.5 g, 47.3 mmoles) in 30 ml of water is introduced into a 100 ml two-necked flask. Potassium cyanide (1.85 g, 35.5 mmoles) is added and tetrahydro-4H-thiopyran-4-one (2.7 g, 23.6 mmoles) is introduced dropwise. The pH of the medium is adjusted to 11 with a few drops of soda (10%). After 24 hours under agitation at ambient temperature, extraction with ether (3×80 ml) is carried out, the combined organic phases are washed with water (100 ml), dried over Na2SO4, filtered and concentrated to dryness. In this way, a colourless oil is obtained (3.9 g, 17.2 mmoles).

Workup

  1. extractionextraction with ether (3×80 ml)
  2. washthe combined organic phases are washed with water (100 ml)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated to dryness
  6. customIn this way, a colourless oil is obtained (3.9 g, 17.2 mmoles)

Sources & evidence

ORD record
ord-d07a03dcdc9a4c4fa52f7db4d978e1b6
Source dataset
uspto-grants-2002_01
Patent number
US06342511B1

Reaction notes

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