Hydrochloric Acid → 1-[2-(Imidazol-1-yl)ethyl]-4-(3-phenylpropyl)piperidine, dihydrochloride monohydrate

HRID 1599477Notes

Reaction equation

HRID 1599477 reaction equation
C(=O)(O)[O-:2].[Na+].[Cl:6][CH2:7][CH2:8][N:9]1[CH:13]=[CH:12][N:11]=[CH:10]1.[C:14]1([CH2:20][CH2:21][CH2:22][CH:23]2[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[ClH:29]>CCOCC>[OH2:2].[ClH:6].[ClH:29].[N:9]1([CH2:8][CH2:7][N:26]2[CH2:27][CH2:28][CH:23]([CH2:22][CH2:21][CH2:20][C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH2:24][CH2:25]2)[CH:13]=[CH:12][N:11]=[CH:10]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 876784-(3-Phenylpropyl)piperidineHCID 516892Sodium BicarbonateHCID 27575041-(2-Chloroethyl)imidazole

Product 1

HCID 1317206221-[2-(Imidazol-1-yl)ethyl]-4-(3-phenylpropyl)piperidine, dihydrochloride monohydrate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Sodium bicarbonate (2.9 g) was added to a solution of 1-(2-chloroethyl)imidazole (4.0 g) and 4-(3-phenylpropyl)piperidine (6.2 g) in industrial methylated spirits (100 ml) and the reaction mixture heated under reflux for 96 hours. The reaction mixture was then filtered and the filtrate concentrated to give an oil, which was purified by flash chromatography eluting with ethylacetate/methanol/triethylamine (88:10:2). The solid obtained was dissolved in ether, ethereal hydrogen chloride acid was added and the solid precipitated was collected and recrystallised from ethanol/ether to give 1-[2-(imidazol-1-yl)ethyl]-4-(3-phenylpropyl)piperidine, dihydrochloride monohydrate, m.p. 178°-179° C.

Workup

  1. temperaturethe reaction mixture heated
  2. temperatureunder reflux for 96 hours
  3. filtrationThe reaction mixture was then filtered
  4. concentrationthe filtrate concentrated
  5. customto give an oil, which
  6. customwas purified by flash chromatography
  7. washeluting with ethylacetate/methanol/triethylamine (88:10:2)
  8. customThe solid obtained
  9. customthe solid precipitated
  10. customwas collected
  11. customrecrystallised from ethanol/ether

Sources & evidence

ORD record
ord-8e57febe840441159c259e2255af618f
Source dataset
uspto-grants-1998_04
Patent number
US05741800

Reaction notes

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