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

HRID 359388Notes

Reaction equation

HRID 359388 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-3c62edc2b0e34ab7a9f976b4f7ef618b
Source dataset
uspto-grants-1991_03
Patent number
US05001127

Reaction notes

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