Epichlorohydrin → HCID 70046861, compound

HRID 476617Notes

Reaction equation

HRID 476617 reaction equation
[Cl:1][C:2]1[CH:20]=[CH:19][C:5]([CH:6]([N:13]2[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)[C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.[CH2:21]([CH:23]1[O:25][CH2:24]1)[Cl:22].C([O-])(O)=O.[Na+]>CCO>[OH2:25].[Cl:22][CH2:21][CH:23]([OH:25])[CH2:24][N:16]1[CH2:15][CH2:14][N:13]([CH:6]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:20][CH:19]=2)[CH2:18][CH2:17]1.[Cl:22][CH2:21][CH:23]([OH:25])[CH2:24][N:16]1[CH2:15][CH2:14][N:13]([CH:6]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:20][CH:19]=2)[CH2:18][CH2:17]1

Participants

5

Reactant 3

HCID 7835EpichlorohydrinHCID 9340NorchlorcyclizineHCID 516892Sodium Bicarbonate

Product 1

HCID 70046861HCID 70046861, compoundYield 26.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

4-Chlorobenzhydrylpiperazine (14.34 g, 50 mmol) in EtOH (150 mL) was added to epichlorohydrin (3.92 mL, 50 mmol) in ethanol (25 mL) and NaHCO3 (4.2 g, 50 mmol) over 45 min at 0° C. under nitrogen. After 20 h, the EtOH was removed in vacuo and the residue eluted through silica gel using 50% methanol: methylene chloride to give the pure product (3.40 g, 18.3%) as a white solid, mp 72°-74° C. DCI/MS (M+1) 379. 400 MHz 1H NMR (CDCl3) δ: 7.5-7.35 (m, 9H), 4.2 (s, 1H), 3.65 (m, 2H), 2.9 (m, 2H), 2.7-2.6 (m, 8H).

Workup

  1. customthe EtOH was removed in vacuo
  2. washthe residue eluted through silica gel using 50% methanol

Sources & evidence

ORD record
ord-70b4dc0ce78642e7a8f19f60be2c7bfd
Source dataset
uspto-grants-1989_12
Patent number
US04885300

Reaction notes

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