Epichlorohydrin → HCID 15670859, compound

HRID 476616Notes

Reaction equation

HRID 476616 reaction equation
[CH2:1]([N:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1)[C:2]1[CH:10]=[CH:9][C:8]2[O:7][CH2:6][O:5][C:4]=2[CH:3]=1.[CH2:17]([CH:19]1[O:21][CH2:20]1)[Cl:18].C([O-])(O)=O.[Na+]>CCO>[Cl:18][CH2:17][CH:19]([OH:21])[CH2:20][N:14]1[CH2:15][CH2:16][N:11]([CH2:1][C:2]2[CH:10]=[CH:9][C:8]3[O:7][CH2:6][O:5][C:4]=3[CH:3]=2)[CH2:12][CH2:13]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

1-Piperonylpiperazine (11.0 g, 50 mmol) in EtOH (125 mL) was added dropwise to epichlorohydrin (3.9 mL, 50 mmol) in EtOH (25 mL) and NaHCO3 (4.2 g, 50 mmol) 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% methanol: methylene chloride) 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. customremoval of the EtOH in vacuo

Sources & evidence

ORD record
ord-4a0908fcb2394b3098fe65ceb5d50f4e
Source dataset
uspto-grants-1989_12
Patent number
US04885300

Reaction notes

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