1-Bromo-3-chloropropane → Piperazine, 1-(3-chloropropyl)-4-(diphenylmethyl)-

HRID 1518946Notes

Reaction equation

HRID 1518946 reaction equation
[C:1]1([CH:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:27][CH2:28][CH2:29][Cl:30]>CC(C)=O>[C:14]1([CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[N:8]2[CH2:9][CH2:10][N:11]([CH2:27][CH2:28][CH2:29][Cl:30])[CH2:12][CH2:13]2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 70048Benzhydrylpiperazine

Product 1

HCID 10936372Piperazine, 1-(3-chloropropyl)-4-(diphenylmethyl)-

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

In acetone, 1-(diphenylmethyl)piperazine (18.49 g) was dissolved, and potassium carbonate (1.0 eq.) and 1-bromo-3-chloropropane (2.0 eq.) were added thereto, and the obtained mixture was heated to reflux for 3 hours. The salt produced by the reaction was separated by filtration, and the filtrate was then concentrated in vacuo. The residue was purified by silica gel column chromatography (Wakogel C-200, 200 g) and eluted by a mixed solvent of 99 parts of chloroform and 1 part of methanol to obtain 1-[4-(diphenylmethyl)piperazinyl]-3-chloropropane (13.8 g).

Workup

  1. temperaturethe obtained mixture was heated
  2. temperatureto reflux for 3 hours
  3. customThe salt produced by the reaction
  4. customwas separated by filtration
  5. concentrationthe filtrate was then concentrated in vacuo
  6. customThe residue was purified by silica gel column chromatography (Wakogel C-200, 200 g)
  7. washeluted by a mixed solvent of 99 parts of chloroform and 1 part of methanol

Sources & evidence

ORD record
ord-17e946a76465416597d607addfab7fb4
Source dataset
uspto-grants-2015_07
Patent number
US09073861B2

Reaction notes

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