Reaction #955

ord-38cb457f7729445685e412a4fffa8894

Reaction equation

OCCC1CCNCC1
4-hydroxyethyl piperidine
CSC(=N)NC(=O)OCc1ccccc1
N-benzyloxycarbonyl-S-methyl isothiourea
→
N=C(NC(=O)OCc1ccccc1)N1CCC(CCO)CC1
title compound
Yield 41.0%
N=C(NC(=O)OCc1ccccc1)N1CCC(CCO)CC1
1-Benzyloxycarbonylamidino-4-hydroxyethyl piperidine
Yield 41.0%

Reactants

OCCC1CCNCC1
4-hydroxyethyl piperidine
CSC(=N)NC(=O)OCc1ccccc1
N-benzyloxycarbonyl-S-methyl isothiourea

Reagents

None

Solvents

CC#N
acetonitrile

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Temperaturewas refluxed overnight
  2. 2
    OtherEvaporation and flash chromatography on silica gel with ethyl acetate

Procedure

A mixture of 6.2 g (0.028 mol) of 4-hydroxyethyl piperidine and 3.6 g (0.028 mol) of N-benzyloxycarbonyl-S-methyl isothiourea in 50 ml of acetonitrile was refluxed overnight. Evaporation and flash chromatography on silica gel with ethyl acetate gave 3.5 g (41%) of the title compound.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05723444uspto-grants-1998_03