4-Nitrophenethyl bromide → 1,3-dihydro-1-oxo-1'-[2-(4-nitrophenyl)-1-ethyl]-spiro[2H-indene-2,4'-piperidine]

HRID 1781359Notes

Reaction equation

HRID 1781359 reaction equation
[O:1]=[C:2]1[C:10]2([CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)[CH2:9][C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2.[N+:16]([C:19]1[CH:27]=[CH:26][C:22]([CH2:23][CH2:24]Br)=[CH:21][CH:20]=1)([O-:18])=[O:17].C(=O)(O)[O-].[Na+]>C(O)C>[O:1]=[C:2]1[C:10]2([CH2:15][CH2:14][N:13]([CH2:24][CH2:23][C:22]3[CH:21]=[CH:20][C:19]([N+:16]([O-:18])=[O:17])=[CH:27][CH:26]=3)[CH2:12][CH2:11]2)[CH2:9][C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2

Participants

5

Reactant 3

HCID 792664-Nitrophenethyl bromideHCID 516892Sodium BicarbonateHCID 19085830Spiro[indene-2,4'-piperidin]-1(3H)-one

Product 1

HCID 677244561,3-dihydro-1-oxo-1'-[2-(4-nitrophenyl)-1-ethyl]-spiro[2H-indene-2,4'-piperidine]Yield 58%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 0.60 g (3.0 moles) 1,3-dihydro-1-oxospiro[2H-indene-2,4'-piperidine], 0.71 g (3.1 mmoles) 4-nitrophenethyl bromide, and 0.28 g (3.3 mmoles) sodium bicarbonate in 3 ml ethanol was heated at reflux for 6 hours. The solvent was removed in vacuo and the residue was partitioned between 20 ml ethyl acetate and 5 ml dilute bicarbonate solution. The layers were separated and the aqueous layer was extracted with 20 ml ethyl acetate. The combined extract was washed wth 5 ml water and brine, dried, and the solvent was removed in vacuo to give 1.08 g crude product as a gum. This was purified by flash chromatography on silica gel eluting with methanol:chloroform (2:98). The material obtained was crystallized from 1:10 methylene chloride:ether to give 0.61 g (58%) product, m.p. 187°-188° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 6 hours
  3. customThe solvent was removed in vacuo
  4. customthe residue was partitioned between 20 ml ethyl acetate and 5 ml dilute bicarbonate solution
  5. customThe layers were separated
  6. extractionthe aqueous layer was extracted with 20 ml ethyl acetate
  7. extractionThe combined extract
  8. washwas washed wth 5 ml water and brine
  9. customdried
  10. customthe solvent was removed in vacuo
  11. customto give 1.08 g crude product as a gum
  12. customThis was purified by flash chromatography on silica gel eluting with methanol:chloroform (2:98)
  13. customThe material obtained
  14. customwas crystallized from 1:10 methylene chloride

Sources & evidence

ORD record
ord-605cac8cff47459890dbd04581014144
Source dataset
uspto-grants-1997_05
Patent number
US05633247

Reaction notes

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