Hydrochloric Acid → 1-Piperazinecarboxamide, N-((dimethylamino)carbonyl)-N-methyl-4-(1-methylethyl)-, monohydrochloride

HRID 979048Notes

Reaction equation

HRID 979048 reaction equation
[ClH:1].[CH3:2][N:3]([C:12]([N:14]([CH3:16])[CH3:15])=[O:13])[C:4]([N:6]1[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1)=[O:5].C(=O)([O-])[O-].[Na+].[Na+].[CH:23](Br)([CH3:25])[CH3:24].Cl>C(O)C>[ClH:1].[CH:23]([N:9]1[CH2:8][CH2:7][N:6]([C:4](=[O:5])[N:3]([CH3:2])[C:12]([N:14]([CH3:16])[CH3:15])=[O:13])[CH2:11][CH2:10]1)([CH3:25])[CH3:24]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 63582-BromopropaneHCID 10340Sodium CarbonateHCID 13094265HCID 13094265, compound

Product 1

HCID 30669791-Piperazinecarboxamide, N-((dimethylamino)carbonyl)-N-methyl-4-(1-methylethyl)-, monohydrochlorideYield 65.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 20 ml of ethanol, were added 5.0 g of 1-(2,4,4-trimethylallophanoyl)piperazine hydrochloride and 3.7 g of sodium carbonate. To the resulting mixture, was added dropwise with stirring 2.5 g of isopropyl bromide. The mixture was allowed to react under reflux for 8 hours and the precipitate was removed by filtration. The filtrate was concentrated and the residue was purified with a silica gel column to obtain an oil. This oil was converted to hydrochloride in the customary way and recrystallized from ethanol to obtain 3.8 g (65% yield) of 1-(isopropyl)-4-(2,4,4-trimethylallophanoyl)piperazine hydrochloride having a melting point of 213°-215° C.

Workup

  1. additionTo the resulting mixture, was added dropwise
  2. customto react
  3. temperatureunder reflux for 8 hours
  4. customthe precipitate was removed by filtration
  5. concentrationThe filtrate was concentrated
  6. customthe residue was purified with a silica gel column
  7. customto obtain an oil
  8. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-a473463f5ffb407abca5674709b84438
Source dataset
uspto-grants-1987_05
Patent number
US04666911

Reaction notes

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