1,2-Diaminocyclohexane → N,N'-bis(chloroacetyl)-trans-1,2-diaminocyclohexane

HRID 363414Notes

Reaction equation

HRID 363414 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]1[NH2:8].[Cl:9][CH2:10][C:11](Cl)=[O:12].[C:14](=[O:17])([O-])[O-].[K+].[K+].[CH:20](Cl)(Cl)[Cl:21]>O>[Cl:21][CH2:20][C:14]([NH:1][C@@H:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C@H:3]1[NH:8][C:11](=[O:12])[CH2:10][Cl:9])=[O:17]

Participants

6

Reactant 4

HCID 46101,2-DiaminocyclohexaneHCID 6212Chloroform2×HCID 6577Chloroacetyl chlorideHCID 11430Potassium Carbonate

Product 1

HCID 10061487N,N'-bis(chloroacetyl)-trans-1,2-diaminocyclohexaneYield 67%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A 12 liter three-neck flask equipped with a magnetic stirbar and two 1 liter dropping funnels was charged with 1,2-diaminocyclohexane (35.0 g, 0.310 mol) dissolved in chloroform (375 ml) and water (185 ml). The two dropping funnels were charged individually with chloroacetyl chloride (75 ml, 0.94 mol) in chloroform (440 ml) and potassium carbonate (120.5 g, 0.87 mol) in water (4 l), added in four portions during the addition. The flask was cooled in an ice salt bath and addition of the reagents was carried out over 2 h. The ice salt bath was removed, water (600 ml) was added, and the reaction mixture was stirred for 2.5 h. The mixture was separated and the water layer was extracted with chloroform several times. The combined chloroform layers were washed with water and then brine. The organic layer was dried (sodium sulfate) and concentrated in vacuo to yield an off-white solid. The solid was washed with ether to yield 55.32 g (67% yield) of a white solid after drying in vacuo: mp 202°-3° C.; 1H NMR (CDCl3) δ 1.27-1.50 (m, 4 H), 1.75-1.95 (m, 2 H), 2.03-2.20 (m, 2 H), 3.72-3.87 (m, 2 H), 4.05 (s, 4 H), 6.81 (br s, 2 H).

Workup

  1. additionadded in four portions during the addition
  2. temperatureThe flask was cooled in an ice salt bath
  3. additionaddition of the reagents
  4. customThe ice salt bath was removed
  5. additionwater (600 ml) was added
  6. customThe mixture was separated
  7. extractionthe water layer was extracted with chloroform several times
  8. washThe combined chloroform layers were washed with water
  9. dry with materialThe organic layer was dried (sodium sulfate)
  10. concentrationconcentrated in vacuo
  11. customto yield an off-white solid
  12. washThe solid was washed with ether

Sources & evidence

ORD record
ord-83aaa248dfb74f75bf61013f11d46b5b
Source dataset
uspto-grants-1999_02
Patent number
US05874421

Reaction notes

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