Hydrochloric Acid → (1-Benzyl-4-piperidyl)methanamine

HRID 54556

Reaction equation

HRID 54556 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([C:14](=O)[NH2:15])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl>O1CCCC1>[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][NH2:15])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 7831561-Benzylpiperidine-4-carboxamide

Product 1

HCID 1514444(1-Benzyl-4-piperidyl)methanamineYield 59.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 1-benzyl-4-carbamoylpiperidine (2.5 g) in tetrahydrofuran (10 ml) was added dropwise to 1N solution of diborane-tetrahydrofuran complex in tetrahydrofuran (34.3 ml) at 0° C. and then the mixture was refluxed for 3 hours. After cooling to room temperature, 6N hydrochloric acid (10 ml) was added thereto. The mixture was stirred overnight and concentrated in vacuo. The residue was dissolved in ethyl acetate and made basic with 5N sodium hydroxide. The separated organic layer was washed with water and brine and dried over magnesium sulfate, and evaporated in vacuo to give (1-benzylpiperidin-4-yl)methylamine (1.4 g) as an oil.

Workup

  1. temperaturethe mixture was refluxed for 3 hours
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washThe separated organic layer was washed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-018b6baf30414d4e9bc50e685a97c250
Source dataset
uspto-grants-1997_04
Patent number
US05622976

Linked notes

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