Sodium Hydroxide → HCID 13938993, compound

HRID 2309261Notes

Reaction equation

HRID 2309261 reaction equation
[CH:1]([NH:5][C:6](=[O:9])[CH2:7]Cl)([CH2:3][CH3:4])[CH3:2].[OH-:10].[Na+]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[CH:1]([N:5]1[CH2:7][C:6](=[O:10])[N:5]([CH:1]([CH2:3][CH3:4])[CH3:2])[CH2:7][C:6]1=[O:9])([CH2:3][CH3:4])[CH3:2]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 3138632N-(sec-butyl)-2-chloroacetamide

Product 1

HCID 13938993HCID 13938993, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 1140TolueneSolvent

Conditions

Temperature
75 °C

Procedure

Toluene (75 ml), N-sec-butyl-2-chloracetamide (14.9 g, 0.10 mol), tetrabutylammonium hydrogen sulfate (1.7 g, 5×10-3 mol), and powdered sodium hydroxide (16.0 g, 0.40 mol) were charged into a 500 ml Morton flask equipped with a mechanical stirrer, thermometer and condenser. The reaction mixture was vigorously stirred and heated to 75° C. for one hour. The reaction mixture was cooled, filtered and solvent removed under reduced pressure. The resulting solids were recrystallized from ether to give 7.0 g (62%) of 1,4-di-sec-butyl-2,5-diketopiperazine as an off-white colored solid, mp 95.5°-97.5° C. Analytical results on the product were as follows: 1H NMR (CDCl3, TMS, 90 MHz) δ4.54 (septet, J=7 Hz, 2H), 3.78 (s, 4H), 1.45 (q, J=6 Hz, 4H), 1.10 (d, J=6 Hz, 6H), 0.83 (t, J=7 Hz, 6H) Mass spectrum, m/e =226 (parent). Anal. calcd. for C12H22N2O2 :C, 63.68; H, 9.80; N, 12.38. Found: C, 63,51; H, 9.82; N, 12.30.

Workup

  1. customequipped with a mechanical stirrer
  2. temperatureThe reaction mixture was cooled
  3. filtrationfiltered
  4. customsolvent removed under reduced pressure
  5. customThe resulting solids were recrystallized from ether

Sources & evidence

ORD record
ord-1bf52cf2961349eb855c097d2c360444
Source dataset
uspto-grants-1987_09
Patent number
US04694082

Reaction notes

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