Acetone Cyanohydrin → HCID 59280235, compound

HRID 1942444Notes

Reaction equation

HRID 1942444 reaction equation
CS([CH:5]1[CH2:10][CH2:9][C:8](=O)[CH2:7][CH2:6]1)(=O)=O.[N:12]1[CH:17]=[CH:16][CH:15]=[C:14]([CH2:18][NH2:19])[CH:13]=1.CC(O)([C:23]#[N:24])C.C(N(CC)CC)C>CO>[N:12]1[CH:17]=[CH:16][CH:15]=[C:14]([CH2:18][N:19]2[CH:8]3[CH2:9][CH2:10][C:5]2([C:23]#[N:24])[CH2:6][CH2:7]3)[CH:13]=1

Participants

6

Reactant 4

HCID 6406Acetone CyanohydrinHCID 8471TriethylamineHCID 310183-PyridinemethanamineHCID 669406684-(Methylsulfonyl)cyclohexanone

Product 1

HCID 59280235HCID 59280235, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
100 °C

Procedure

In a dry pressure resistant vessel of 20 ml, 1.0 g (5.20 mmole) 4-methanesulphonylcyclohexanone, 0.56 g (5.20 mmole) 3-picolylamine, 0.89 g (10.4 mmole) acetonecyanohydrin and 1.06 g (10.4 mmole) triethylamine were dissolved in 16 ml dry methanol. The vessel was closed and heated for 50 hours at 100° C. Methanol was then evaporated and the residue was redissolved in dichloromethane, washed with a saturated NaHCO3 solution, dried over MgSO4, filtered and evaporated. The residue was further purified by means of column chromatography. 7-(pyridin-3-ylmethyl)-7-aza-bicyclo[2.2.1]heptane-1-carbonitrile (structural formula below) was thus obtained in a 50% yield and characterised by proton (1H-NMR) and carbon (13C-NMR) nuclear magnetic resonance, infrared (IR) spectrophotometry and mass spectrum (MSES) as follows:

Workup

  1. customThe vessel was closed
  2. customMethanol was then evaporated
  3. dissolutionthe residue was redissolved in dichloromethane
  4. washwashed with a saturated NaHCO3 solution
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was further purified by means of column chromatography

Sources & evidence

ORD record
ord-cfb08e32f1374d80965530ff06c961d0
Source dataset
uspto-grants-2013_03
Patent number
US08389561B2

Reaction notes

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