Hydrochloric Acid → 4-(4-Oxocyclohexyl)-1,3-oxazinan-2-one

HRID 2175512Notes

Reaction equation

HRID 2175512 reaction equation
O1[C:5]2([CH2:10][CH2:9][CH:8]([CH:11]3[CH2:16][CH2:15][O:14][C:13](=[O:17])[NH:12]3)[CH2:7][CH2:6]2)[O:4]CC1.C(#N)C.Cl.C(=O)(O)[O-].[NH4+]>O>[O:4]=[C:5]1[CH2:10][CH2:9][CH:8]([CH:11]2[CH2:16][CH2:15][O:14][C:13](=[O:17])[NH:12]2)[CH2:7][CH2:6]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6342AcetonitrileHCID 14013Ammonium BicarbonateHCID 585625634-(1,4-Dioxaspiro[4.5]decan-8-yl)-1,3-oxazinan-2-one

Product 1

HCID 585625224-(4-Oxocyclohexyl)-1,3-oxazinan-2-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 250 mL round bottom flask was charge with 4-(1,4-dioxaspiro[4.5]decan-8-yl)-1,3-oxazinan-2-one (1.39 g, 5.76 mmol) and acetonitrile (96 mL). A solution of concentrated HCl (6.4 mL) in water (19 mL) was added to the mixture. The mixture was stirred at room temperature for 20 h. Saturated aqueous ammonium bicarbonate was added until the pH was >7. The mixture was extracted with ethyl acetate. Dry organic layer with MgSO4, filter, and concentrate in vacuo to give the target material as a clear oil.

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. filtrationDry organic layer with MgSO4, filter
  3. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-1ce8b7506cf24b20a01424b5185baad9
Source dataset
uspto-grants-2015_06
Patent number
US09062048B2

Reaction notes

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