Epichlorohydrin → HCID 15670859, compound

HRID 2210719Notes

Reaction equation

HRID 2210719 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-6625e060b47440e7a4a5d04603106c74
Source dataset
uspto-grants-1995_10
Patent number
USRE035072

Reaction notes

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