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

HRID 2210717Notes

Reaction equation

HRID 2210717 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-9fde9d9f018047cba0dcc463f8915885
Source dataset
uspto-grants-1995_10
Patent number
USRE035072

Reaction notes

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