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

HRID 373632Notes

Reaction equation

HRID 373632 reaction equation
[CH2:1]([CH:3]1[O:5][CH2:4]1)[Cl:2].C([O-])(O)=O.[Na+].[C:11]1([CH:17]([N:24]2[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]2)[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>C(O)C>[Cl:2][CH2:1][CH:3]([OH:5])[CH2:4][N:27]1[CH2:28][CH2:29][N:24]([CH:17]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:25][CH2:26]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

To a mixture of epichlorohydrin (5.1 mL, 0.065 mL) in ethanol (13 mL) and anhydrous NaHCO3 (0.065 mol, 5,46 g) at 0° C., diphenylmethylpiperazine (16.4 g, 0.065 mol) in ethanol (250 mL) was added dropwise 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 was removed from the filtrate in vacuo giving a white-yellow solid (21.5 g). This solid after trituration with Et2 (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 was removed from the filtrate in vacuo

Sources & evidence

ORD record
ord-b8432ada9edb4bfaac42bd03aa83f892
Source dataset
uspto-grants-1992_11
Patent number
US05164390

Reaction notes

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