Pyridine → Heptopargil

HRID 1389410Notes

Reaction equation

HRID 1389410 reaction equation
Cl.[CH2:2]([CH:5]1C=CC=C[O:6]1)[C:3]#C.[CH3:11][C:12]12[C:18]([CH3:20])([CH3:19])[CH:15]([CH2:16][CH2:17]1)[CH2:14][C:13]2=O.[N:22]1C=CC=CC=1>C(O)C>[CH2:5]([O:6][N:22]=[C:13]1[CH2:14][CH:15]2[C:18]([CH3:20])([CH3:19])[C:12]1([CH3:11])[CH2:17][CH2:16]2)[C:2]#[CH:3]

Participants

5

Reactant 3

HCID 1049PyridineHCID 2537CamphorHCID 86737430HCID 86737430, compound

Product 1

HCID 52692HeptopargilYield 74%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

59.0 g (0.55 moles) of propargyloxamine hydrochloride are added to a solution of 76 g (0.5 moles) of (±)-1,7,7-trimethyl-bicyclo[2,2,1]heptane-2-one in 225 ml of pyridine and 450 ml of dry ethanol. The reaction mixture is boiled for 3 hours and then it is evaporated in vacuo. The residue is diluted with water, and the aqueous mixture is extracted with dichloroethane. The dichloroethane solution is evaporated, and the residue is subjected to fractional distillation in vacuo. 76.0 g (74.0%) of (±)-2-(propargyloxyimino)-1,7,7-trimethyl-bicyclo[2,2,1]heptane are obtained as a light yellow oil; b.p.: 92° C./1.0 mm Hg, nD20 =1.4956.

Workup

  1. customit is evaporated in vacuo
  2. additionThe residue is diluted with water
  3. extractionthe aqueous mixture is extracted with dichloroethane
  4. customThe dichloroethane solution is evaporated
  5. distillationthe residue is subjected to fractional distillation in vacuo

Sources & evidence

ORD record
ord-a8411769db6245c2a62aead80e5cc045
Source dataset
uspto-grants-1981_01
Patent number
US04244888

Reaction notes

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