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

HRID 1169697Notes

Reaction equation

HRID 1169697 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-c34a5a81c8994c7fbf53942b7c02ffaf
Source dataset
uspto-grants-2010_11
Patent number
US07825134B2

Reaction notes

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