Ammonia → 4-Amino-2,2,6,6-tetramethylpiperidine

HRID 1414345Notes

Reaction equation

HRID 1414345 reaction equation
[NH3:1].[Cl-].[NH4+:3].[H][H].[CH3:6][C:7](=[CH:9][C:10](=O)[CH:11]=[C:12]([CH3:14])[CH3:13])[CH3:8]>CO>[NH2:1][CH:10]1[CH2:9][C:7]([CH3:8])([CH3:6])[NH:3][C:12]([CH3:14])([CH3:13])[CH2:11]1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 10438PhoroneHCID 25517Ammonium ChlorideHCID 178418361HCID 178418361, compound2×

Product 1

HCID 375244-Amino-2,2,6,6-tetramethylpiperidine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
200 °C

Procedure

100 ml of methanol, 150 ml of liquid ammonia, 1 g of ammonium chloride and 20 g of a standard commercial hydrogenation catalyst (Raney nickel) were introduced into a 0.7 litre capacity hydrogenation autoclave. The autoclave was heated to 200°C under a hydrogen pressure of about 20 to about 40 atms, so that the hydrogen pressure settled at a level of approximately 80 atms. A solution of 100 g of phorone in 100 ml of methanol was then pumped in over a period of about 1 hour. After about 30 minutes, the fall in the hydrogen pressure and, hence, hydrogenation were over. After cooling, the autoclave was vented and the reaction solution filtered off from the catalyst. Fractional distillation of the reaction solution yielded 52 g (46% of the theoretical yield) of 4-amino-2,2,6,6-tetramethyl piperidine with a boiling point of 86° to 90°C/15 Torr.

Workup

  1. customwas then pumped in over a period of about 1 hour
  2. temperatureAfter cooling
  3. filtrationthe reaction solution filtered off from the catalyst
  4. distillationFractional distillation of the reaction solution
  5. customyielded 52 g (46% of the

Sources & evidence

ORD record
ord-0ef813e4904347dca2e0904a73de89b2
Source dataset
uspto-grants-1977_01
Patent number
US04001250

Reaction notes

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