Sulfuric Acid → HCID 86738825, compound

HRID 355024

Reaction equation

HRID 355024 reaction equation
ClCCN(N=O)[C:5](N=[N+]=[N-])=[O:6].NN1[CH2:18][CH2:17]CCC1.[CH3:19][CH2:20][CH2:21][CH2:22][CH3:23].[OH:24]S(O)(=O)=O>ClCCl>[CH:5]([O:6][CH2:17][CH3:18])=[O:24].[CH3:19][CH2:20][CH2:21][CH2:22][CH3:23]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 8003PentaneHCID 166581-AminopiperidineHCID 10654895N-(2-chloroethyl)-N-nitrosocarbamoylazide

Product 1

HCID 86738825HCID 86738825, compoundYield 21%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 0.1 mole N-(2-chloroethyl)-N-nitrosocarbamoylazide in 75 ml dichloromethane is added in drops at -5 degC. (°C.) under stirring within 2 hours a solution of 0.2 mole N-aminopiperidine in 20 ml of a mixture of 4 parts by volume dichloromethane and 1 part by volume n-pentane. After the addition, the stirring is continued for one hour and a whitish-yellow precipitate is obtained. Subsequently it is shaken out with the same volume of 0.1 N H2SO4. The organic phase is dried over Na2SO4 and concentrated on the rotary evaporator. From ethyl formate/n-pentane we obtain on standing in the deep freezer yellow crystals which are homogeneous in thin-layer chromatography, after recrystallization from the same solvent mixture (silicagel foils, solvent system n-pentane/diethylether/dichloromethane 5:2:2)

Workup

  1. additionAfter the addition
  2. customa whitish-yellow precipitate is obtained
  3. dry with materialThe organic phase is dried over Na2SO4
  4. concentrationconcentrated on the rotary evaporator

Sources & evidence

ORD record
ord-e453c6e61c9b4fa3a7ff75464caa5402
Source dataset
uspto-grants-1983_03
Patent number
US04377687

Linked notes

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