Acetic Acid → HCID 87172952, compound

HRID 2167751Notes

Reaction equation

HRID 2167751 reaction equation
[CH3:1][O:2][N:3]1[C:8]([CH3:10])([CH3:9])[CH2:7][C:6]([C:12]#[N:13])([OH:11])[CH2:5][C:4]1([CH3:15])[CH3:14].[CH3:16][C:17]([CH3:19])=O.S(=O)(=O)(O)[OH:21].[C:25]([O-:28])(O)=O.[Na+].[C:30](O)(=O)[CH3:31]>>[CH3:1][O:2][N:3]1[C:8]([CH3:10])([CH3:9])[CH2:7][C:6]2([O:11][C:17]([CH3:19])([CH3:16])[N:13]([CH2:30][CH:31]3[CH2:25][O:28]3)[C:12]2=[O:21])[CH2:5][C:4]1([CH3:15])[CH3:14]

Participants

6

Reactant 5

HCID 176Acetic AcidHCID 180AcetoneHCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 87280060HCID 87280060, compound

Product 1

HCID 87172952HCID 87172952, compound

Conditions

Temperature
70 °C

Procedure

1.0 g of 1-methoxy-2,2,6,6-tetramethyl-4-cyano-4-hydroxypiperidine is dissolved in 2.0 g acetic acid and 0.65 g acetone is added. 0.8 g conc. sulfuric acid is added and the reaction mixture is stirred at 70° C. for 18 h. The reaction mixture is added to 40 ml saturated NaHCO3 solution, and extracted with ethyl acetate. The organic phase is washed with H2O and subsequently dried over sodium sulfate. The solvent is removed in vacuo to leave 0.71 g of a tan residue. After washing the residue with n-hexane, 8-methoxy-2,2,7,7,9,9-hexamethyl-1-oxa-3,8-diaza-spiro[4.5]decan-4-one is obtained as a white solid.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic phase is washed with H2O
  3. dry with materialsubsequently dried over sodium sulfate
  4. customThe solvent is removed in vacuo

Sources & evidence

ORD record
ord-4b109df707f046ecbc1d57005ea0b216
Source dataset
uspto-grants-2015_06
Patent number
US09045480B2

Reaction notes

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