N,N'-Dimethylethylenediamine → 3-(2-Hydroxyethyl)-1,4-dimethyl-2-piperazinone

HRID 462503Notes

Reaction equation

HRID 462503 reaction equation
[CH3:1][NH:2][CH2:3][CH2:4][NH:5][CH3:6].Br[CH:8]1[CH2:13][CH2:12][O:11][C:9]1=[O:10].C(N(CC)CC)C>O1CCCC1>[OH:11][CH2:12][CH2:13][CH:8]1[N:5]([CH3:6])[CH2:4][CH2:3][N:2]([CH3:1])[C:9]1=[O:10]

Participants

5

Reactant 3

HCID 8070N,N'-DimethylethylenediamineHCID 8471TriethylamineHCID 954632(3H)-Furanone, 3-bromodihydro-

Product 1

HCID 133767393-(2-Hydroxyethyl)-1,4-dimethyl-2-piperazinone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The mixture of sym. dimethylethylenediamine (1 eq, 53 g), bromobutyrolactone (1 eq, 100 g) and triethylamine (1 eq, 120 ml) in 1000 mL of tetrahydrofuran was refluxed overnight. The crude precipitate was filtered and thoroughly washed with diethyl ether. The ether was evaporated and the residue was purified by elution through a silica gel column using 2% (v/v) methanol in chloroform to obtain the title compound. A small sample was converted into a picrate and crystallized from methanol to obtain the picrate salt of the title compound: mp 157°-159° C.; IR (KBr) 3220, 1650, 1565 and 1330 cm-1 ; UV max (MeOH) 353 nm (ε 18090); and NMR (DMSO-d6) δ 2.1 (m, 2H), 2.9 and 2.93 (singlets, 6H), 3.5 (m, 6H), 3.95 (m, 1H), and 8.55 (s, 2H).

Workup

  1. additionThe mixture of sym
  2. filtrationThe crude precipitate was filtered
  3. washthoroughly washed with diethyl ether
  4. customThe ether was evaporated
  5. customthe residue was purified by elution through a silica gel column

Sources & evidence

ORD record
ord-b6b76f1c62444b79be428a68c615f64c
Source dataset
uspto-grants-1985_05
Patent number
US04515949

Reaction notes

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