Acetonitrile → HCID 178442347, compound

HRID 1198840Notes

Reaction equation

HRID 1198840 reaction equation
[CH2:1]([C:7]1[CH:8]=[CH:9][C:10]([C:13]2[CH:18]=[CH:17][C:16]([C@H:19]3[CH2:24][CH2:23][C@H:22]([CH2:25][O:26]CC4C=CC(OC)=CC=4)[CH2:21][CH2:20]3)=[CH:15][CH:14]=2)=[N:11][CH:12]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].C(#N)C.[N+]([O-])([O-])=O.[NH4+]>O>[CH2:1]([C:7]1[CH:8]=[CH:9][C:10]([C:13]2[CH:18]=[CH:17][C:16]([C@H:19]3[CH2:20][CH2:21][C@H:22]([CH2:25][OH:26])[CH2:23][CH2:24]3)=[CH:15][CH:14]=2)=[N:11][CH:12]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 22985Ammonium nitrateHCID 178442348HCID 178442348, compound

Product 1

HCID 178442347HCID 178442347, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of 0.485 g of 5-hexyl-2-[p-(trans-4-(p-anisyloxymethyl)cyclohexyl)phenyl]pyridine, 9.6 ml of acetonitrile and 2.4 ml of water is treated at 0° C. with 1.25 g of cer-(IV) ammonium nitrate. After 10 minutes the reaction mixture is diluted with water and extracted with diethyl ether. The organic phase is washed several times with water, then dried over magnesium sulphate and evaporated. Purification of the residue by chromatography on silica gel gives 5-hexyl-2-[p-(trans-4-(hydroxymethyl)-cyclohexyl)phenyl]pyridine.

Workup

  1. extractionextracted with diethyl ether
  2. washThe organic phase is washed several times with water
  3. dry with materialdried over magnesium sulphate
  4. customevaporated
  5. customPurification of the residue by chromatography on silica gel

Sources & evidence

ORD record
ord-fc505a67072348ca8f14b2d468d7bf85
Source dataset
uspto-grants-1990_02
Patent number
US04898455

Reaction notes

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