4-(Aminomethyl)piperidine → HCID 22719679, compound

HRID 322485Notes

Reaction equation

HRID 322485 reaction equation
[CH:1]1[CH:6]=[C:5]2[CH:7]=[CH:8][CH:9]=[C:10]([CH2:11][N:12]=[C:13]=[S:14])[C:4]2=[CH:3][CH:2]=1.[NH2:15][CH2:16][CH:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1.CO.C(Cl)(Cl)Cl>CO.C1COCC1>[C:10]1([CH2:11][NH:12][C:13]([NH:15][CH2:16][CH:17]2[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]2)=[S:14])[C:4]2[C:5](=[CH:6][CH:1]=[CH:2][CH:3]=2)[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 235274-(Aminomethyl)piperidineHCID 1401821-Naphthalenemethyl isothiocyanateHCID 21584188Chloroform methanol

Product 1

HCID 22719679HCID 22719679, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of 1-naphthalenemethylisothiocyanate (2.8 g, 13.6 mmol) in 100 ml of MeOH-THF solution (1:1 mixture) was added 4-aminomethylpiperidine (3.1 ml, 27.0 mmol) in a portion and the resulting solution was stirred at reflux for 12 h. The reaction mixture was concentrated in vacuo, yielding oily mixture which was subjected to column chromatography (10% MeOH/CHCl3) to yield 2.3 g (48%) of the desired product as an oil.

Workup

  1. temperatureat reflux for 12 h
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customyielding oily mixture which

Sources & evidence

ORD record
ord-cc0e0f22e4c441ff87750cc400109375
Source dataset
uspto-grants-2001_04
Patent number
US06211241B1

Reaction notes

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