Epichlorohydrin → 4-(3-Chloro-2-hydroxypropyl)-1-diphenylmethylpiperazine

HRID 476614Notes

Reaction equation

HRID 476614 reaction equation
[C:1]1([CH:7]([N:14]2[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:20]([CH:22]1[O:24][CH2:23]1)[Cl:21].C([O-])(O)=O.[Na+]>C(O)C>[Cl:21][CH2:20][CH:22]([OH:24])[CH2:23][N:17]1[CH2:16][CH2:15][N:14]([CH:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:19][CH2:18]1

Participants

5

Reactant 3

HCID 7835EpichlorohydrinHCID 70048BenzhydrylpiperazineHCID 516892Sodium Bicarbonate

Product 1

HCID 103601754-(3-Chloro-2-hydroxypropyl)-1-diphenylmethylpiperazine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Diphenylmethylpiperazine (16.4 g, 0.065 mol) in ethanol (250 mL) was added dropwise to epichlorohydrin (5.1 mL, 0.065 mL) in ethanol (13 mL) with anhydrous NaHCO3 (0.065 mol, 5,46 g) at 0° C., over 45 min at room temperature under N2. After 17 h the NaHCO3 was removed by filtration via a sintered glass funnel and the ethanol removed from the filtrate in vacuo giving a white-yellow solid (21.5 g). This solid after triturating with Et2O (300 mL) gave a precipitate which was filtered and dried in vacuo to give the pure product (5.11 g, 22.8%) mp 114°-116° C. DCI/MS (M+1) 345. 400 MHz 1H NMR (CDCl3) δ: 7.2-7.4 (m, 10H), 4.2 (s, 1H), 3.9 (m, 1H), 3.55-3.7 (m, 2H), 2.7 (m, 2H), 2.45 (m, 8H).

Workup

  1. customAfter 17 h the NaHCO3 was removed by filtration via a sintered glass funnel
  2. customthe ethanol removed from the filtrate in vacuo

Sources & evidence

ORD record
ord-9afb6c93b8df40d28722c806b8ca897b
Source dataset
uspto-grants-1989_12
Patent number
US04885300

Reaction notes

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