Epichlorohydrin → HCID 11777838, compound

HRID 359389Notes

Reaction equation

HRID 359389 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-1493e05698c942658e35600858bb15a9
Source dataset
uspto-grants-1991_03
Patent number
US05001127

Reaction notes

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