1,6-Hexanediamine, 2,2,4-trimethyl- → HCID 20544070, compound

HRID 2285710Notes

Reaction equation

HRID 2285710 reaction equation
[O:1]=[C:2]1[CH2:6][CH2:5][CH2:4][N:3]1[CH2:7][C:8]([O:10]CC)=O.[CH3:13][C:14]([CH3:23])([CH2:17][CH:18]([CH3:22])[CH2:19][CH2:20][NH2:21])[CH2:15][NH2:16]>CO>[CH3:13][C:14]([CH3:23])([CH2:17][CH:18]([CH3:22])[CH2:19][CH:20]([C:8](=[O:10])[CH2:7][N:3]1[CH2:4][CH2:5][CH2:6][C:2]1=[O:1])[NH2:21])[CH:15]([C:8](=[O:10])[CH2:7][N:3]1[CH2:4][CH2:5][CH2:6][C:2]1=[O:1])[NH2:16]

Participants

4

Reactant 2

HCID 929501,6-Hexanediamine, 2,2,4-trimethyl-HCID 109094Ethyl 2-oxopyrrolidine-1-acetate

Product 1

HCID 20544070HCID 20544070, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

8.55 g (0.05 mol) of ethyl 2-oxo-1-pyrrolidineacetate and 3.95 g (0.025 mol) of 2,2,4-trimethyl-1,6-diaminohexane are boiled in 5 ml of absolute methanol for 22 hours, moisture being excluded. After evaporating off the solvent, the residue is chromatographed on silica gel from methanol/water (80:30). Chromatography is then carried out a second time from methanol/water/acetic acid (20:7.5:2.5), and finally the water and the acetic acid are removed by chromatography on aluminium oxide. The product is syrupy with nD54 1.5095.

Workup

  1. customAfter evaporating off the solvent
  2. customthe residue is chromatographed on silica gel from methanol/water (80:30)
  3. customfinally the water and the acetic acid are removed by chromatography on aluminium oxide

Sources & evidence

ORD record
ord-c41cf692eb054832a3b7ef83d4191919
Source dataset
uspto-grants-1982_04
Patent number
US04324787

Reaction notes

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