4-Acetamido-1-cyclohexyloxy-2,2,6,6-tetramethylpiperidine → 4-Amino-1-cyclohexyloxy-2,2,6,6-tetramethylpiperidine

HRID 1590947Notes

Reaction equation

HRID 1590947 reaction equation
C([NH:4][CH:5]1[CH2:10][C:9]([CH3:12])([CH3:11])[N:8]([O:13][CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)[C:7]([CH3:21])([CH3:20])[CH2:6]1)(=O)C>O.Cl>[NH2:4][CH:5]1[CH2:10][C:9]([CH3:11])([CH3:12])[N:8]([O:13][CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)[C:7]([CH3:21])([CH3:20])[CH2:6]1

Participants

4

Reactant 1

HCID 233721204-Acetamido-1-cyclohexyloxy-2,2,6,6-tetramethylpiperidine

Product 1

HCID 222779844-Amino-1-cyclohexyloxy-2,2,6,6-tetramethylpiperidine

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Procedure

A solution of 5.0 g of the acetamide from Example 47 in 7.5 ml of water and 7.5 ml of conc. hydrochloric acid is heated at reflux for 10 hours. The reaction mixture is then quenched with saturated sodium carbonate and extracted with ethyl acetate. The combined organic extracts are washed with water, brine, dried (MgSO4) and evaporated to leave a light brown oil. Distillation (Kugelrohr, 140° C. @ 1.5 mm) affords the title compound as a clear colorless oil.

Workup

  1. temperatureat reflux for 10 hours
  2. customThe reaction mixture is then quenched with saturated sodium carbonate
  3. extractionextracted with ethyl acetate
  4. washThe combined organic extracts are washed with water, brine
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customto leave a light brown oil
  8. distillationDistillation (Kugelrohr, 140° C. @ 1.5 mm)

Sources & evidence

ORD record
ord-20400bae19bc435083a1307f1c5118eb
Source dataset
uspto-grants-1993_04
Patent number
US05204473

Reaction notes

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