Hydrochloric Acid → Lauryl 3-[N-(1-Octyloxy-2,2,6,6-tetramethylpiperidin-4-yl)-N-hydroxyamino]propionate

HRID 1654988Notes

Reaction equation

HRID 1654988 reaction equation
[CH2:1]([O:9][N:10]1[C:15]([CH3:17])([CH3:16])[CH2:14][C:13](=[N:18][OH:19])[CH2:12][C:11]1([CH3:21])[CH3:20])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].Cl.[H][H].[C:25]([O:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41])(=[O:28])[CH:26]=[CH2:27]>[Pt].CO>[CH2:1]([O:9][N:10]1[C:11]([CH3:20])([CH3:21])[CH2:12][CH:13]([N:18]([CH2:27][CH2:26][C:25]([O:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41])=[O:28])[OH:19])[CH2:14][C:15]1([CH3:17])[CH3:16])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 75084Lauryl acrylateHCID 229026981-Octyloxy-2,2,6,6-tetramethylpiperidin-4-one oximeHCID 178418361HCID 178418361, compound

Product 1

HCID 22902716Lauryl 3-[N-(1-Octyloxy-2,2,6,6-tetramethylpiperidin-4-yl)-N-hydroxyamino]propionateYield 57.8%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 1-octyloxy-2,2,6,6-tetramethylpiperidin-4-one oxime (10.0 g, 35.4 mmol) (a mixture of octyloxy isomers) 5.5 ml of concentrated hydrochloric acid and 130 ml of methanol is subjected to 3 atmospheres of hydrogen over 5% platinum on carbon for 18 hours. The reaction mixture is filtered through celite and then concentrated. The residue is partitioned between ethyl acetate and aqueous potassium carbonate. The organic layer is washed with water and brine, dried over anhydrous sodium sulfate and finally concentrated to a total volume of about 150 ml. Lauryl acrylate (7.7 g, 32 mmol) is added. After a two-hour reaction time, the reaction mixture is concentrated and the crude product purified by flash chromatography on silica gel (9:1, hexane:ethyl acetate) to yield 10.0 g (52% yield) of a clear oil.

Workup

  1. filtrationThe reaction mixture is filtered through celite
  2. concentrationconcentrated
  3. customThe residue is partitioned between ethyl acetate and aqueous potassium carbonate
  4. washThe organic layer is washed with water and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationfinally concentrated to a total volume of about 150 ml
  7. customAfter a two-hour reaction time
  8. concentrationthe reaction mixture is concentrated
  9. customthe crude product purified by flash chromatography on silica gel (9:1, hexane:ethyl acetate)

Sources & evidence

ORD record
ord-4813ff571b7042f19799c940e5aa0912
Source dataset
uspto-grants-1995_04
Patent number
US05410047

Reaction notes

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