4-Piperidineethanol → benzyl N-[4-(2-hydroxyethyl)piperidine-1-carboximidoyl]carbamate

HRID 859

Reaction equation

HRID 859 reaction equation
[OH:1][CH2:2][CH2:3][CH:4]1[CH2:9][CH2:8][NH:7][CH2:6][CH2:5]1.[CH2:10]([O:17][C:18]([NH:20][C:21](=[NH:24])SC)=[O:19])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>C(#N)C>[CH2:10]([O:17][C:18]([NH:20][C:21]([N:7]1[CH2:8][CH2:9][CH:4]([CH2:3][CH2:2][OH:1])[CH2:5][CH2:6]1)=[NH:24])=[O:19])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 739534-PiperidineethanolHCID 140362141Benzyl [amino(methylsulfanyl)methylene]carbamate

Product 1

HCID 140379078benzyl N-[4-(2-hydroxyethyl)piperidine-1-carboximidoyl]carbamateYield 41%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

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.

Workup

  1. temperaturewas refluxed overnight
  2. customEvaporation and flash chromatography on silica gel with ethyl acetate

Sources & evidence

ORD record
ord-38cb457f7729445685e412a4fffa8894
Source dataset
uspto-grants-1998_03
Patent number
US05723444

Linked notes

Loading…