1,3-Propanediamine → N-(1-Benzylpiperidin-4-yl)propane-1,3-diamine

HRID 25967

Reaction equation

HRID 25967 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][NH2:5].[CH2:6]([N:13]1[CH2:18][CH2:17][C:16](=O)[CH2:15][CH2:14]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>C(O)C>[NH2:1][CH2:2][CH2:3][CH2:4][NH:5][CH:16]1[CH2:15][CH2:14][N:13]([CH2:6][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH2:18][CH2:17]1

Participants

4

Reactant 2

HCID 4281,3-PropanediamineHCID 192201-Benzyl-4-piperidone

Product 1

HCID 3017248N-(1-Benzylpiperidin-4-yl)propane-1,3-diamine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The starting material is prepared as follows: To the ice cooled stirred solution of 62.5 ml of 1,3-diaminopropane in 100 ml of ethanol, 30 g of 1-benzyl-4-piperidone are added dropwise. The mixture is hydrogenated over 2 g of pre-reduced platinum oxide at 50° and 2.7 atm. for 9 hours. After theoretical hydrogen-uptake the catalyst is filtered off, the filtrate evaporated, the residue distilled and the fraction boiling at 145°-160°/0.2 mmHg collected, to yield the 4-(3-aminopropylamino)-1-benzylpiperidine.

Workup

  1. customThe starting material is prepared
  2. additionare added dropwise
  3. filtrationAfter theoretical hydrogen-uptake the catalyst is filtered off
  4. customthe filtrate evaporated
  5. distillationthe residue distilled
  6. customthe fraction boiling at 145°-160°/0.2 mmHg collected

Sources & evidence

ORD record
ord-c893534eda664bd0b93af5aadf21ad9e
Source dataset
uspto-grants-1979_04
Patent number
US04147786

Linked notes

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