Hydrochloric Acid → 1-Hydroxy-4-cyclopropanecarbonyloxy-2,2,6,6-tetramethylpiperidine hydrochloride

HRID 2117391Notes

Reaction equation

HRID 2117391 reaction equation
[OH:1][N:2]1[C:7]([CH3:9])([CH3:8])[CH2:6][CH:5]([O:10][C:11]([CH:13]2[CH2:15][CH2:14]2)=[O:12])[CH2:4][C:3]1([CH3:17])[CH3:16].[ClH:18]>C(O)C>[ClH:18].[OH:1][N:2]1[C:7]([CH3:9])([CH3:8])[CH2:6][CH:5]([O:10][C:11]([CH:13]2[CH2:14][CH2:15]2)=[O:12])[CH2:4][C:3]1([CH3:17])[CH3:16]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 10131000Ot-551

Product 1

HCID 114828181-Hydroxy-4-cyclopropanecarbonyloxy-2,2,6,6-tetramethylpiperidine hydrochloride

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The nitroxide of Example 5a (2.2 g, 9.15 mmol) was added to a solution of saturated hydrogen chloride in ethanol (20 mL). The red color disappeared quickly and the resulting yellow colored solution was boiled to give clear colorless solution. The solution was concentrated in vacuo, dissolved in 100 mL ethyl acetate and was washed with saturated NaHCO3 to obtain the hydroxylamine free-base. The ethyl acetate layer was separated, acidified with ethereal HCl, and concentrated to give white solid, which was recrystallized from ethanol (10 mL) as a white crystalline solid 1.15 g (4.13 mmol, 45.1%). m.p. 224-228° C. (dec.).

Workup

  1. customto give clear colorless solution
  2. concentrationThe solution was concentrated in vacuo
  3. dissolutiondissolved in 100 mL ethyl acetate
  4. washwas washed with saturated NaHCO3

Sources & evidence

ORD record
ord-82a6fc9851444e93837045d26df9de36
Source dataset
uspto-grants-2008_10
Patent number
US07442711B2

Reaction notes

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