4-Nitrophenethyl bromide → HCID 19759194, compound

HRID 1086844Notes

Reaction equation

HRID 1086844 reaction equation
[ClH:1].[NH:2]1[CH2:7][CH2:6][CH:5]([CH:8]2[CH2:16][C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]2=[O:17])[CH2:4][CH2:3]1.[N+:18]([C:21]1[CH:29]=[CH:28][C:24]([CH2:25][CH2:26]Br)=[CH:23][CH:22]=1)([O-:20])=[O:19].C(=O)(O)[O-].[Na+]>C(O)C>[ClH:1].[N+:18]([C:21]1[CH:29]=[CH:28][C:24]([CH2:25][CH2:26][N:2]2[CH2:3][CH2:4][CH:5]([CH:8]3[CH2:16][C:15]4[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=4)[C:9]3=[O:17])[CH2:6][CH2:7]2)=[CH:23][CH:22]=1)([O-:20])=[O:19]

Participants

5

Reactant 3

HCID 792664-Nitrophenethyl bromideHCID 516892Sodium BicarbonateHCID 19759205HCID 19759205, compound

Product 1

HCID 19759194HCID 19759194, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 0.46 g (0.00183 mol) of 2-(4-piperidyl)-1-indanone hydrochloride, 0.578 g (0.00251 mol) of p-nitrophenethyl bromide, 0.422 g (0.00502 mol) sodium bicarbonate and 20 mL of ethanol was stirred and refluxed for 72 hours. The ethanol was removed by evaporation, and the residue was partitioned between ethyl acetate and water. The ethyl acetate phase was washed with water, dried over magnesium sulfate, filtered, and the ethyl acetate removed. The residue was purified by chromatography on silica gel using 2.5% methanol in chloroform as an eluant. Evaporation of the solvent gave a crystalline product that was converted to a hydrochloride salt. Recrystallization from ethanol gave 2-[1-(4-nitrophenethyl)-4-piperidyl]-1-indanone hydrochloride, mp 259°-261° C.

Workup

  1. temperaturerefluxed for 72 hours
  2. customThe ethanol was removed by evaporation
  3. customthe residue was partitioned between ethyl acetate and water
  4. washThe ethyl acetate phase was washed with water
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customthe ethyl acetate removed
  8. customThe residue was purified by chromatography on silica gel using 2.5% methanol in chloroform as an eluant
  9. customEvaporation of the solvent
  10. customgave a crystalline product that
  11. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-cd2c18aed5804789934597fcca72b072
Source dataset
uspto-grants-1991_07
Patent number
US05032598

Reaction notes

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