Ammonia → 1-(3-Phenyl-[1,2,4]oxadiazol-5-yl)-piperidin-4-one

HRID 68757Notes

Reaction equation

HRID 68757 reaction equation
[C:1]1([C:7]2[N:11]=[C:10]([N:12]3[CH2:21][CH2:20][C:15]4(OCC[O:16]4)[CH2:14][CH2:13]3)[O:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.N>O>[C:1]1([C:7]2[N:11]=[C:10]([N:12]3[CH2:13][CH2:14][C:15](=[O:16])[CH2:20][CH2:21]3)[O:9][N:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 209526538-(3-Phenyl-1,2,4-oxadiazol-5-yl)-1,4-dioxa-8-azaspiro[4.5]decane

Product 1

HCID 682902121-(3-Phenyl-[1,2,4]oxadiazol-5-yl)-piperidin-4-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 8-(3-phenyl-[1,2,4]oxadiazol-5-yl)-1,4-dioxa-8-aza-spiro[4.5]decane (660 mg), conc. aqueous HCl (5 mL) and water (5 mL) is kept at room temperature over night. The mixture is basified with conc. aqueous ammonia and the precipitate is filtered off and dissolved in dichloromethane. The resulting solution is dried over Na2SO4 and concentrated in vacuo to give the title compound. TLC: rf=0.33 (silica gel, hexane/ethyl acetate 2:1); Mass spectrum (ESI+): m/z=244 [M+H]+.

Workup

  1. waitis kept at room temperature over night
  2. filtrationthe precipitate is filtered off
  3. dissolutiondissolved in dichloromethane
  4. dry with materialThe resulting solution is dried over Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4bf4a52a7c9c44a6950c58f3f18ba9bf
Source dataset
uspto-grants-2014_09
Patent number
US08822471B2

Reaction notes

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