4-(Aminomethyl)piperidine → 4-[2,4-Dimethyl-1,5-di-(3,3-dimethylnorborn-2-yl)-3-pentylaminomethyl]piperidine

HRID 258785

Reaction equation

HRID 258785 reaction equation
[CH3:1][CH:2]([C:13](=O)[CH:14]([CH3:25])[CH2:15]C1C(C)(C)C2CC1CC2)[CH2:3][CH:4]1[C:9]([CH3:11])([CH3:10])[CH:8]2[CH2:12][CH:5]1[CH2:6][CH2:7]2.[NH2:27][CH2:28][CH:29]1[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1.[H][H]>O=[Pt]=O.C(O)C>[CH3:25][CH:14]([CH:13]([NH:27][CH:28]([CH:29]1[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1)[CH:4]1[C:9]([CH3:11])([CH3:10])[CH:8]2[CH2:12][CH:5]1[CH2:6][CH2:7]2)[CH:2]([CH3:1])[CH2:3][CH:4]1[C:9]([CH3:11])([CH3:10])[CH:8]2[CH2:12][CH:5]1[CH2:6][CH2:7]2)[CH3:15]

Participants

6

Reactant 3

HCID 235274-(Aminomethyl)piperidineHCID 214257072,4-Dimethyl-1,5-di-(3,3-dimethylnorborn-2-yl)-3-pentanoneHCID 178418361HCID 178418361, compound

Product 1

HCID 681236934-[2,4-Dimethyl-1,5-di-(3,3-dimethylnorborn-2-yl)-3-pentylaminomethyl]piperidine

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 702EthanolSolvent

Procedure

A mixture of 2,4-dimethyl-1,5-di-(3,3-dimethylnorborn-2-yl)-3-pentanone (g., 0.1 mole) and 4-aminomethylpiperidine (34.2 g., 0.3 mole) 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-(3,3-dimethylnorborn-2-yl)-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-ecd5d6c851ed49639d779e2f14a35b3b
Source dataset
uspto-grants-1977_07
Patent number
US04033748

Linked notes

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