Hydrochloric Acid → 4-Amino-N-octyloxy-2,2,6,6-tetramethylpiperidine

HRID 1756849Notes

Reaction equation

HRID 1756849 reaction equation
[CH2:1]([O:9][N:10]1[C:15]([CH3:17])([CH3:16])[CH2:14][CH:13]([NH:18]C(=O)C)[CH2:12][C:11]1([CH3:23])[CH3:22])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].Cl>>[NH2:18][CH:13]1[CH2:14][C:15]([CH3:16])([CH3:17])[N:10]([O:9][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])[C:11]([CH3:22])([CH3:23])[CH2:12]1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 23372128N-(1-Octyloxy-2,2,6,6-tetramethylpiperidin-4-yl)acetamide

Product 1

HCID 233720934-Amino-N-octyloxy-2,2,6,6-tetramethylpiperidineYield 83%

Procedure

A mixture of 40.0 grams (0.123 mol) of N-(1-octyloxy-2,2,6,6-tetramethylpiperidin-4-yl)acetamide and 6N hydrochloric acid is heated at reflux for three hours. The reaction mixture is cooled and extracted with 2×150 ml). The aqueous layer is made basic and extracted with 3:1 ether:dichloromethane (3×150 ml). The three organic extracts are combined, dried over anhydrous magnesium sulfate and then concentrated to an oil. Purification by Kugelrohr distillation at 110°-120° C./0.5 mm affords 28.9 grams (83% yield) of the title compound as a pale yellow oil.

Workup

  1. temperatureis heated
  2. temperatureat reflux for three hours
  3. temperatureThe reaction mixture is cooled
  4. extractionextracted with 2×150 ml)
  5. extractionextracted with 3:1 ether
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated to an oil
  8. customPurification
  9. distillationby Kugelrohr distillation at 110°-120° C./0.5 mm

Sources & evidence

ORD record
ord-f9397cf34d014e3a95d5800b351bf96b
Source dataset
uspto-grants-1995_08
Patent number
US05442071

Reaction notes

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