1,4-Dioxa-8-azaspiro(4.5)decane → (3-Methyl-1,2,4-oxadiazol-5-yl)-4-piperidone ethylene ketal

HRID 1418375Notes

Reaction equation

HRID 1418375 reaction equation
[CH3:1][C:2]1[N:6]=[C:5](C(Cl)(Cl)Cl)[O:4][N:3]=1.[CH2:11]1[O:20][C:14]2([CH2:19][CH2:18][NH:17][CH2:16][CH2:15]2)[O:13][CH2:12]1>C(O)C>[CH2:11]1[O:20][C:14]2([CH2:19][CH2:18][N:17]([C:5]3[O:4][N:3]=[C:2]([CH3:1])[N:6]=3)[CH2:16][CH2:15]2)[O:13][CH2:12]1

Participants

4

Reactant 2

HCID 674351,4-Dioxa-8-azaspiro(4.5)decaneHCID 709533-Methyl-5-(trichloromethyl)-1,2,4-oxadiazole

Product 1

HCID 57153768(3-Methyl-1,2,4-oxadiazol-5-yl)-4-piperidone ethylene ketalYield 19.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-Methyl-5-trichloromethyl-1,2,4-oxadiazole (Moussebois and Eloy, Helv. Chim. Acta 1964, 47, 838) (1 g, 5 mmol) and 4-piperidone ethylene ketal (1.5 g, 10 mmol) in ethanol (20 ml) were heated reflux overnight. The solvent was evaporated and the residue taken up in dichloromethane and filtered. The filtrate was washed with dilute HCl, dried over sodium sulphate and evaporated to leave a pale yellow oil (0.22 g). The acid washing was neutralised with solid sodium bicarbonate and extracted with dichloromethane. Evaporation gave further oil (0.17 g, total 0.39 g), MS (+EI) 225 (M+).

Workup

  1. temperaturereflux overnight
  2. customThe solvent was evaporated
  3. filtrationfiltered
  4. washThe filtrate was washed with dilute HCl
  5. dry with materialdried over sodium sulphate
  6. customevaporated

Sources & evidence

ORD record
ord-13487dec1f804d92a366f3492c25bde9
Source dataset
uspto-grants-1999_03
Patent number
US05883102

Reaction notes

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