Sodium Hydroxide → HCID 13938990, compound

HRID 2309260Notes

Reaction equation

HRID 2309260 reaction equation
[CH:1]([NH:4][C:5](=[O:8])[CH2:6]Cl)([CH3:3])[CH3:2].[OH-:9].[Na+]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.C(Cl)Cl>[CH:1]([N:4]1[CH2:6][C:5](=[O:9])[N:4]([CH:1]([CH3:3])[CH3:2])[CH2:6][C:5]1=[O:8])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 761712-chloro-N-(1-methylethyl)acetamide

Product 1

HCID 13938990HCID 13938990, compoundYield 36%

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

The compound N-isopropyl-α-chloroacetamide (2.71 g; 0.02 mole) and benzyltriethylammonium chloride (0.09 g) were dissolved in methylene chloride (50 ml) in a 100 ml flask. A 50% by weight sodium hydroxide solution (16 g) was added to the mixture, and the mixture was stirred vigorously at 40° C. for three days. Thereafter, the organic phase was separated, dried and evaporated. The residue of the evaporation (found to be four parts product per part starting material) was recrystallized from ethyl alcohol to yield 0.7 g (36%) of 1,4-diisopropyl-2,5-diketopiperazine. All spectral data were consistent with this structure.

Workup

  1. customThereafter, the organic phase was separated
  2. customdried
  3. customevaporated
  4. customThe residue of the evaporation (found to be four parts product per part starting material)
  5. customwas recrystallized from ethyl alcohol

Sources & evidence

ORD record
ord-7ac6897899064305bfbc1bfc1f557460
Source dataset
uspto-grants-1987_09
Patent number
US04694082

Reaction notes

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