4-(Aminomethyl)piperidine → HCID 70621136, compound

HRID 1679108Notes

Reaction equation

HRID 1679108 reaction equation
[CH3:1][CH:2]([C:11](=O)[CH:12]([CH3:21])[CH2:13]C1C=CC(C)=CC=1)[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([CH3:10])=[CH:6][CH:5]=1.[NH2:23][CH2:24][CH:25]1[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1.[H][H]>O=[Pt]=O.C(O)C>[CH3:21][CH:12]([CH:11]([NH:23][CH:24]([CH:25]1[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1)[C:7]1[CH:8]=[CH:9][C:4]([CH3:3])=[CH:5][CH:6]=1)[CH:2]([CH3:1])[CH2:3][C:4]1[CH:5]=[CH:6][C:7]([CH3:10])=[CH:8][CH:9]=1)[CH3:13]

Participants

6

Reactant 3

HCID 235274-(Aminomethyl)piperidineHCID 20363681HCID 20363681, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 70621136HCID 70621136, compound

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 702EthanolSolvent

Procedure

A mixture of 2,4-dimethyl-1,5-di-(4-methylphenyl)-3-pentanone (29.4 g., 0.1 mole) and 4-aminomethylpiperidine (34.2 g., 0.3 mole) in 250 ml. ethanol is hydrogenated with PtO2 at room temperature and 40 psi hydrogen pressure. The 2.5 g. platinum catalyst is filtered off and the ethanol removed under reduced pressure. The residual oil is dissolved in ether and the ether solution washed several times with water to remove the excess 4-aminomethylpiperidine. The ether extracts are dried over anhydrous sodium sulfate and concentrated under vacuum to leave 4-[2,4-dimethyl-1,5-di-(4-methylphenyl)-3-pentylaminomethyl]piperidine.

Workup

  1. filtrationplatinum catalyst is filtered off
  2. customthe ethanol removed under reduced pressure
  3. dissolutionThe residual oil is dissolved in ether
  4. washthe ether solution washed several times with water
  5. customto remove the excess 4-aminomethylpiperidine
  6. dry with materialThe ether extracts are dried over anhydrous sodium sulfate
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-a490d07c5f154432a8ab8230e0c21481
Source dataset
uspto-grants-1978_03
Patent number
US04079059

Reaction notes

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