1-Benzyl-4-piperidylamine → HCID 178505158, compound

HRID 1059347Notes

Reaction equation

HRID 1059347 reaction equation
[CH3:1][S:2]([N:5]=[CH:6]OCC)(=[O:4])=[O:3].[NH2:10][CH:11]1[CH2:16][CH2:15][N:14]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:13][CH2:12]1>C(OCC)C>[CH3:1][S:2]([N:5]=[CH:6][NH:10][CH:11]1[CH2:16][CH2:15][N:14]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:13][CH2:12]1)(=[O:3])=[O:4]

Participants

4

Reactant 2

HCID 4158521-Benzyl-4-piperidylamineHCID 54392285Ethyl (methanesulfonyl)methanimidate

Product 1

HCID 178505158HCID 178505158, compoundYield 39.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Into a solution of 760 mg of ethyl N-methanesulfonyl-formimidate in diethyl ether (20 ml) was dropped 0.95 g of 4-amino-1-benzylpiperidine at room temperature. After stirring for 2 hours, the crystals thus precipitated were filtered and washed with diethyl ether to thereby give 580 mg of N2-methanesulfonyl-N1-(1-benzylpiperidin-4-yl)formamidine as colorless needles. These crystals were dissolved in 30 ml of methanol and 500 mg of 10% palladium-carbon was added thereto. Then the resulting mixture was stirred in a hydrogen atmosphere under atmospheric pressure for 1 hour followed by filtration through celite. After distilling off the solvent under reduced pressure, the residue was recrystallized from acetone/ethyl acetate to thereby give 310 mg of the title compound as colorless needles.

Workup

  1. customthe crystals thus precipitated
  2. filtrationwere filtered
  3. washwashed with diethyl ether

Sources & evidence

ORD record
ord-1b8f01b7c619488cbeede27e00cb2a58
Source dataset
uspto-grants-2003_02
Patent number
US06518423B1

Reaction notes

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