Acetic Acid → Acetic acid--2-(2,2-dicyclohexylethyl)piperidine (1/1)

HRID 1701178Notes

Reaction equation

HRID 1701178 reaction equation
[C:1]1([C:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:21]([OH:24])(=[O:23])[CH3:22]>>[C:21]([OH:24])(=[O:23])[CH3:22].[CH:1]1([CH:7]([CH:15]2[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]2)[CH2:8][CH:9]2[CH2:14][CH2:13][CH2:12][CH2:11][NH:10]2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

3

Reactant 2

HCID 176Acetic AcidHCID 3012122-(2,2-diphenylethenyl)pyridine

Product 1

HCID 70588582Acetic acid--2-(2,2-dicyclohexylethyl)piperidine (1/1)

Conditions

Temperature
115 °C

Procedure

To a nitrogen-purged ten gallon autoclave is added a slurry of 400 g. of a 5 percent rhodium-on-carbon catalyst (Engelhard Industries) followed by a warm (50° C.) solution of glacial acetic acid and 4.0 kg (15.5 moles) of 2-(2,2-diphenylethenyl)pyridine. The charging system is rinsed using an additional 3.5 liters of glacial acetic acid. The system is purged with nitrogen and then hydrogen gas is introduced to a pressure of 40 atmospheres. The reaction mixture is stirred and heated to a temperature of about 115° C. Hydrogenation is continued at this temperature until no further hydrogen is taken up by the reaction mixture, usually a period of three to four hours. The reaction mixture is cooled to 30°-40° C. and the catalyst removed by filtration. The autoclave is rinsed several times with acetic acid which is then used to wash the catalyst. The combined filtrates are concentrated in vacuo to obtain an oily residue of 2-(2,2-dicyclohexylethyl)piperidine acetate.

Workup

  1. customTo a nitrogen-purged ten gallon autoclave
  2. additionis added a slurry of 400 g
  3. washThe charging system is rinsed
  4. customThe system is purged with nitrogen
  5. additionhydrogen gas is introduced to a pressure of 40 atmospheres
  6. waitis taken up by the reaction mixture, usually a period of three to four hours
  7. temperatureThe reaction mixture is cooled to 30°-40° C.
  8. customthe catalyst removed by filtration
  9. washThe autoclave is rinsed several times with acetic acid which
  10. washto wash the catalyst
  11. concentrationThe combined filtrates are concentrated in vacuo

Sources & evidence

ORD record
ord-37b3d06d80a34f588e4ee00b1833a552
Source dataset
uspto-grants-1980_03
Patent number
US04191828

Reaction notes

Loading…