1,2-Epoxybutane → HCID 57964197, compound

HRID 2403546Notes

Reaction equation

HRID 2403546 reaction equation
Cl.Cl.[Cl:3][C:4]1[C:9]([Cl:10])=[CH:8][CH:7]=[CH:6][C:5]=1[N:11]1[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][CH:19]2[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]2)[CH2:13][CH2:12]1.C(=O)([O-])[O-].[K+].[K+].[CH2:31]([CH:33]1[CH2:35][O:34]1)[CH3:32]>C(O)(C)C>[Cl:3][C:4]1[C:9]([Cl:10])=[CH:8][CH:7]=[CH:6][C:5]=1[N:11]1[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][CH:19]2[CH2:24][CH2:23][N:22]([CH2:35][CH:33]([OH:34])[CH2:31][CH3:32])[CH2:21][CH2:20]2)[CH2:13][CH2:12]1

Participants

5

Reactant 3

HCID 78341,2-EpoxybutaneHCID 11430Potassium CarbonateHCID 131731753HCID 131731753, compound

Product 1

HCID 57964197HCID 57964197, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A suspension of 0.41 g (1 mmol) of 1-(2,3-dichlorophenyl)-4-(2-piperidin-4-ylethyl)piperazine, dihydrochloride in 25 mL of isopropanol and 0.29 g (2.1 mmol) of potassium carbonate is stirred for 30 minutes then 0.08 g (1.1 mmol of 2-ethyloxirane is added. The suspension is stirred to reflux overnight. The precipitate is filtered and the solution is concentrated under reduced pressure. The residue is dissolved in ethyl acetate, washed with water and with brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue is purified over 10 g of silica gel (dichloromethane/methanol 90/10) to give 0.2 g (50%) of 1-(4-{2-[4-(2,3-dichlorophenyl)piperazin-1-yl]ethyl}piperidin-1-yl)butan-2-ol as an oil that crystallizes upon standing.

Workup

  1. stirringThe suspension is stirred
  2. temperatureto reflux overnight
  3. filtrationThe precipitate is filtered
  4. concentrationthe solution is concentrated under reduced pressure
  5. dissolutionThe residue is dissolved in ethyl acetate
  6. washwashed with water and with brine
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe residue is purified over 10 g of silica gel (dichloromethane/methanol 90/10)

Sources & evidence

ORD record
ord-c743d9e54a6148f29b1287c7efb39058
Source dataset
uspto-grants-2014_08
Patent number
US08802678B2

Reaction notes

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