Epichlorohydrin → HCID 11777838, compound

HRID 476615Notes

Reaction equation

HRID 476615 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 epichlorohydrin (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 MHz 1H NMR (CDCl3) δ: 7.3 (m, 5H), 4.95 (m, 1H), 4.5 & 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-30e9dde06a334f5a9ebacd0be9cbeb46
Source dataset
uspto-grants-1989_12
Patent number
US04885300

Reaction notes

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