Epichlorohydrin → HCID 11777838, compound

HRID 2210718Notes

Reaction equation

HRID 2210718 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:14]([CH:16]1[O:18][CH2:17]1)[Cl:15].C([O-])(O)=O.[Na+]>CCO>[Cl:15][CH2:14][CH:16]([OH:18])[CH2:17][N:11]1[CH2:12][CH2:13][N:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:9][CH2:10]1

Participants

5

Reactant 3

HCID 7835EpichlorohydrinHCID 759941-BenzylpiperazineHCID 516892Sodium Bicarbonate

Product 1

HCID 11777838HCID 11777838, compoundYield 75.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

1-Benzylpiperazine (8.66 mL, 50 mmol) in EtOH (100 mL) was added dropwise to epichiorohydrin (3.92 mL, 50 mmol) in EtOH (25 mL) with NaHCO3 (4.2 g, 50 mmol) over 30 min at 0° C. under nitrogen. After 16 h the EtOH was removed in vacuo and the crude product eluted through silica gel (5% methanol: methylene chloride) to give pure product (10.12 g, 75.3%) as an amber oil. DCI/MS (M+1) 269. 400 HMz 1H NMR (CDCl3) δ:7.3 (m, 5H), 4.95 (m, 1H),4.& 4.6(m,2H), 3.95(m,1H),3.6(m,2H),3.5(s,2H),2.7(m,4H),2.4(m, 4H).

Workup

  1. customAfter 16 h the EtOH was removed in vacuo
  2. washthe crude product eluted through silica gel (5% methanol: methylene chloride)

Sources & evidence

ORD record
ord-91d94983881f4f40adb5838f85a31aa3
Source dataset
uspto-grants-1995_10
Patent number
USRE035072

Reaction notes

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