Epichlorohydrin → HCID 70046861, compound

HRID 373633Notes

Reaction equation

HRID 373633 reaction equation
[CH2:1]([CH:3]1[O:5][CH2:4]1)[Cl:2].[Cl:6][C:7]1[CH:25]=[CH:24][C:10]([CH:11]([N:18]2[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]2)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:9][CH:8]=1>C(O)C>[OH2:5].[Cl:2][CH2:1][CH:3]([OH:5])[CH2:4][N:21]1[CH2:20][CH2:19][N:18]([CH:11]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:10]2[CH:9]=[CH:8][C:7]([Cl:6])=[CH:25][CH:24]=2)[CH2:23][CH2:22]1.[Cl:2][CH2:1][CH:3]([OH:5])[CH2:4][N:21]1[CH2:20][CH2:19][N:18]([CH:11]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:10]2[CH:9]=[CH:8][C:7]([Cl:6])=[CH:25][CH:24]=2)[CH2:23][CH2:22]1

Participants

4

Reactant 2

HCID 7835EpichlorohydrinHCID 9340Norchlorcyclizine

Product 1

HCID 70046861HCID 70046861, compoundYield 26.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a mixture of epichlorohydrin (3.92 mL, 50 mmol) in ethanol (25 mL) and NAHCO3 (4.2 g, 50 mmol) 4-chlorobenzhydryl piperazine (14.34 g, 50 mmol) in EtOH (150 mL) was added dropwise over 45 min at 0° C. under nitrogen. After 20 h, the EtOH was removed in vacuo and the residue was eluted through silica gel using 50% MeOH:CH2Cl2 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. additionwas added dropwise over 45 min at 0° C. under nitrogen
  2. customthe EtOH was removed in vacuo
  3. washthe residue was eluted through silica gel using 50% MeOH

Sources & evidence

ORD record
ord-7bb27de0c35547a29d7a4bd389ee4881
Source dataset
uspto-grants-1992_11
Patent number
US05164390

Reaction notes

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