Water → HCID 15117213, compound

HRID 1029611Notes

Reaction equation

HRID 1029611 reaction equation
[C:1]([C:4]1(O)[CH2:9][CH2:8][N:7]([C:10]([O:12][CH2:13][CH:14]=[CH2:15])=[O:11])[CH2:6][CH2:5]1)(=[O:3])[CH3:2].S(Cl)(Cl)=O.C(OCC)(=O)C.O>N1C=CC=CC=1>[C:1]([C:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][CH2:13][CH:14]=[CH2:15])=[O:11])[CH2:6][CH:5]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 24386Thionyl ChlorideHCID 15117212HCID 15117212, compound

Product 1

HCID 15117213HCID 15117213, compoundYield 37.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 4-acetyl-1-allyloxycarbonyl-4-hydroxypiperidine (0.2 g) in pyridine (4.0 ml) was added dropwise thionyl chloride (0.12 ml) at -20° C. The resultant mixture was allowed to warm to ambient temperature for 1 hour and stirred for another period of 2 hours. Evaporation of the mixture in vacuo gave a residue which was taken up into a mixture of ethyl acetate and water. The organic layer was separated, washed with brine, dried over magnesium sulfate and evaporated. The residue was chromatographed on silica gel (10 g) eluting with a mixture of n-hexane and ethyl acetate (9:1-1:1 V/V) to give 4-acetyl-1-allyloxycarbonyl-1,2,3,6-tetrahydropyridine (69 mg).

Workup

  1. customEvaporation of the mixture in vacuo
  2. customgave a residue which
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated
  7. customThe residue was chromatographed on silica gel (10 g)
  8. washeluting with a mixture of n-hexane and ethyl acetate (9:1-1:1 V/V)

Sources & evidence

ORD record
ord-c04c003cedeb4bf6a3ad90d89fd35558
Source dataset
uspto-grants-1992_04
Patent number
US05102877

Reaction notes

Loading…