Aziridine → HCID 20373424, compound

HRID 259046Notes

Reaction equation

HRID 259046 reaction equation
[NH2:1][CH2:2][CH2:3][CH:4]1[CH2:9][CH2:8][CH:7]([CH2:10][CH2:11][NH2:12])[CH2:6][CH2:5]1.[CH2:13]1[NH:15][CH2:14]1.[Cl-].[NH4+]>>[NH2:15][CH2:14][CH2:13][NH:1][CH2:2][CH2:3][CH:4]1[CH2:9][CH2:8][CH:7]([CH2:10][CH2:11][NH2:12])[CH2:6][CH2:5]1

Participants

4

Reactant 3

HCID 9033AziridineHCID 25517Ammonium ChlorideHCID 140298721,4-Cyclohexanediethanamine

Product 1

HCID 20373424HCID 20373424, compound

Procedure

1,4-Bis-(2-aminoethyl)cyclohexane (68 gm., 0.4 mole) and ethyleneimine (4.3 gm., 0.1 mole) with 0.4 g. ammonium chloride is mixed in a glasslined pressure reactor and filled with nitrogen to 100 psi. The mixture is shaken and heated to 85°-95° C. for 48 hours. After cooling, it is distilled rapidly free of the salt and then fractionated under high vacuum. The starting diamine is readily distinguished from the triamine product by thin layer chromatography and silica gel using a mixture of 1 volume concentrated aqueous ammonium hydroxide with 4 volume methyl alcohol, the diamine having a much higher Rf.

Workup

  1. additionfilled with nitrogen to 100 psi
  2. temperatureheated to 85°-95° C. for 48 hours
  3. temperatureAfter cooling
  4. distillationit is distilled rapidly free of the salt
  5. additiona mixture of 1 volume concentrated aqueous ammonium hydroxide with 4 volume methyl alcohol

Sources & evidence

ORD record
ord-41a72292c7664ec8b7a8aa38b661ef5d
Source dataset
uspto-grants-1977_07
Patent number
US04035174

Reaction notes

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