Dipropylamine → N-(Piperidin-2-ylmethyl)-N-propylpropan-1-amine

HRID 1073765Notes

Reaction equation

HRID 1073765 reaction equation
Cl.Cl[CH2:3][CH:4]1[CH2:9][CH2:8][CH2:7][CH2:6][NH:5]1.[CH2:10]([NH:13][CH2:14][CH2:15][CH3:16])[CH2:11][CH3:12]>ClCCl>[CH2:10]([N:13]([CH2:3][CH:4]1[CH2:9][CH2:8][CH2:7][CH2:6][NH:5]1)[CH2:14][CH2:15][CH3:16])[CH2:11][CH3:12]

Participants

4

Reactant 2

HCID 8902DipropylamineHCID 221567582-(Chloromethyl)piperidine hydrochloride

Product 1

HCID 10798040N-(Piperidin-2-ylmethyl)-N-propylpropan-1-amine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 170.1 g (1.0 mole) of 2-(chloromethyl)piperidine hydrochloride (M. Rink and H. G. Liem, Arch. Pharm. 292, 165-169 (1959)), 506 g (5.0 mole) of dipropylamine and 1.7 1 of dichloromethane were boiled under reflux for 3 hours, then evaporated in vacuo, and the residue was made alkaline with potassium hydroxide solution with external ice cooling. Exhaustive extraction with t-butyl methyl ether was carried out, and the combined extracts were washed twice with 100 ml of water each time, dried over sodium sulphate, and the solvent was removed by distillation in vacuo. The residue was fractionally distilled under water pump vacuum. Colourless oil of boiling point 108-114° C. (12 mm Hg ). Yield: 108.6 g (55% of theory).

Workup

  1. temperatureunder reflux for 3 hours
  2. customevaporated in vacuo
  3. extractionExhaustive extraction with t-butyl methyl ether
  4. washthe combined extracts were washed twice with 100 ml of water each time
  5. dry with materialdried over sodium sulphate
  6. customthe solvent was removed by distillation in vacuo
  7. distillationThe residue was fractionally distilled under water

Sources & evidence

ORD record
ord-08459017514b478dba3daa5a6216b4d9
Source dataset
uspto-grants-1990_11
Patent number
US04971966

Reaction notes

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