Pyrrolidine → 3,3-Dimethyl-2-methylcarbamyloximino-1-(1-pyrrolidinyl)-butane

HRID 263114Notes

Reaction equation

HRID 263114 reaction equation
Br[C:2](=[N:12][OH:13])[CH:3]([C:8](=[O:11])[NH:9][CH3:10])[C:4]([CH3:7])([CH3:6])[CH3:5].[NH:14]1[CH2:18][CH2:17][CH2:16][CH2:15]1>CCOCC>[CH3:5][C:4]([CH3:7])([CH3:6])[CH:3]([C:8](=[O:11])[NH:9][CH3:10])[C:2](=[N:12][OH:13])[N:14]1[CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 740429621-Bromo-3,3-dimethyl-2-methylcarbamyloximinobutane

Product 1

HCID 867329263,3-Dimethyl-2-methylcarbamyloximino-1-(1-pyrrolidinyl)-butaneYield 97.5%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 12.6 g of 1-bromo-3,3-dimethyl-2-methylcarbamyloximinobutane in 100 ml of anhydrous ether is added, dropwise, 7.8 g (0.11 mol) of pyrrolidine. The mixture is stirred at room temperature for 1 hour and at reflux for 0.5 hour, then cooled and washed with water. The ether solution is separated, dried, and stripped to solvent to give 11.8 g of amber oil which solidifies on standing to an amber solid, m. 43°-46° C. Properties of this and analogous compounds prepared by substantially the same procedure are shown in Table 3.

Workup

  1. temperatureat reflux for 0.5 hour
  2. temperaturecooled
  3. washwashed with water
  4. customThe ether solution is separated
  5. customdried

Sources & evidence

ORD record
ord-a1729c39326a4bb9adc154a79403fc8b
Source dataset
uspto-grants-1979_05
Patent number
US04156082

Reaction notes

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