Hydrochloric Acid → Piperidine-1-propylamine

HRID 235671

Reaction equation

HRID 235671 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[N:7]1([CH2:13][CH2:14][C:15]([NH2:17])=O)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1.Cl>C1COCC1.CO>[N:7]1([CH2:13][CH2:14][CH2:15][NH2:17])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 5667843-(Piperidin-1-yl)propanamideHCID 21226445Aluminium lithium hydride

Product 1

HCID 19049Piperidine-1-propylamine

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To an ice-cooled suspension of LiAlH4 (10.31 g, 0.27 mole) in THF (100 ml), a solution of 1-piperidine-propanamide, 4-(diphenylmethylene) 29.01 g, 0.091 mole) in THF (100 ml) was added dropwise. After stirring for 0.5 hours, the ice-bath was removed, the reaction mixture refluxed for six hours, quenched (EtOAc and 10% NaOH) and the resulting granular precipitate removed by filtration. The filtrate was concentrated to ca 20 ml, dissolved in CHCl3, washed with H2O, and the solvent removed to give a yellow-green oil. This was dissolved in MeOH, treated with HCl gas and the solvent evaporated. The residue crystallized from CH2Cl2 --Et2O to give 1-piperidinepropaneamine, 4-(diphenylmethylene)dihydrochloride hemihydrate as white solid in quantitative yield; mp 249°-252° C.

Workup

  1. customthe ice-bath was removed
  2. temperaturethe reaction mixture refluxed for six hours
  3. customquenched (EtOAc and 10% NaOH)
  4. customthe resulting granular precipitate removed by filtration
  5. concentrationThe filtrate was concentrated to ca 20 ml
  6. dissolutiondissolved in CHCl3
  7. washwashed with H2O
  8. customthe solvent removed
  9. customto give a yellow-green oil
  10. customthe solvent evaporated
  11. customThe residue crystallized from CH2Cl2

Sources & evidence

ORD record
ord-8d9af240f58c422e80f73433d1a3634f
Source dataset
uspto-grants-1987_02
Patent number
US04640925

Linked notes

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