Epichlorohydrin → HCID 15670859, compound

HRID 359395Notes

Reaction equation

HRID 359395 reaction equation
[CH2:1]([CH:3]1[O:5][CH2:4]1)[Cl:2].C([O-])(O)=O.[Na+].[CH2:11]([N:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1)[C:12]1[CH:20]=[CH:19][C:18]2[O:17][CH2:16][O:15][C:14]=2[CH:13]=1>CCO>[Cl:2][CH2:1][CH:3]([OH:5])[CH2:4][N:24]1[CH2:25][CH2:26][N:21]([CH2:11][C:12]2[CH:20]=[CH:19][C:18]3[O:17][CH2:16][O:15][C:14]=3[CH:13]=2)[CH2:22][CH2:23]1

Participants

5

Reactant 3

HCID 7835EpichlorohydrinHCID 944261-PiperonylpiperazineHCID 516892Sodium Bicarbonate

Product 1

HCID 15670859HCID 15670859, compoundYield 26.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a mixture of epichlorohydrin (3.9 mL, 50 mmol) in EtOH (25 mL) and anhydrous NaHCO3 (4.2 g, 50 mmol), 1-piperonylpiperazine (11.0 g, 50 mmol) in EtOH (125 mL) was added dropwise over 45 min at 0° C., under nitrogen. After 16 h and removal of the EtOH in vacuo, the crude material was passed through silica gel (vacuum, 5% MeOH:CH2Cl2) to give pure product (3.85 g, 26.4%) as an amber oil. DCI/MS (M+1) 313. 400 MHz 1H NMR (CDCl3) δ: 7.25 (s, 1H), 6.7-6.8 (m, 2H), 5.9 (s, 2H), 4.6 (m, 1H), 3.9 (m, 1H), 3.5 (m, 2H), 3.4 (s, 2H), 2.4-2.7 (m, 10H).

Workup

  1. additionwas added dropwise over 45 min at 0° C., under nitrogen
  2. customremoval of the EtOH in vacuo

Sources & evidence

ORD record
ord-dc13d5a29ca647b18c1a64f4e2f77a4e
Source dataset
uspto-grants-1991_03
Patent number
US05001127

Reaction notes

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