Sodium Dichromate → 2,7-Bis(1-oxo-4-(1-piperidyl)butyl)-9H-fluoren-9-one

HRID 461964Notes

Reaction equation

HRID 461964 reaction equation
[N:1]1([CH2:7][CH2:8][CH2:9][C:10]([C:12]2[CH:24]=[CH:23][C:22]3[C:21]4[C:16](=[CH:17][C:18]([C:25](=[O:35])[CH2:26][CH2:27][CH2:28][N:29]5[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]5)=[CH:19][CH:20]=4)[CH2:15][C:14]=3[CH:13]=2)=[O:11])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=[O:37].[Na+].[Na+]>C(O)(=O)C>[N:1]1([CH2:7][CH2:8][CH2:9][C:10]([C:12]2[CH:24]=[CH:23][C:22]3[C:21]4[C:16](=[CH:17][C:18]([C:25](=[O:35])[CH2:26][CH2:27][CH2:28][N:29]5[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34]5)=[CH:19][CH:20]=4)[C:15](=[O:37])[C:14]=3[CH:13]=2)=[O:11])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 25408Sodium DichromateHCID 1602411,1'-(9H-Fluorene-2,7-diyl)bis(4-(1-piperidinyl)-1-butanone)

Product 1

HCID 1475842,7-Bis(1-oxo-4-(1-piperidyl)butyl)-9H-fluoren-9-one

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 9.0g (0.019 mole) 2,7-bis(4-piperidinobutyryl)fluorene, prepared in Example 7, 7.54g (0.0253 mole) sodium dichromate and 300 ml of glacial acetic acid was stirred and refluxed for one hour. The reaction mixture was evaporated to semi-dryness and made basic using concentrated ammonium hydroxide. The solid which precipitated was filtered, washed with water, and chromatographed on alumina using chloroform as the eluant. The solvent was removed from the fraction collected, leaving a solid residue which was recrystallized three times from chloroform-acetone to yield the desired product. M.P. 168°-170° C, λmaxCHCl3 281, E1cm1% 1579.

Workup

  1. temperaturerefluxed for one hour
  2. customThe reaction mixture was evaporated to semi-dryness
  3. customThe solid which precipitated
  4. filtrationwas filtered
  5. washwashed with water
  6. customchromatographed on alumina
  7. customThe solvent was removed from the fraction
  8. customcollected
  9. customleaving a solid residue which
  10. customwas recrystallized three times from chloroform-acetone

Sources & evidence

ORD record
ord-c2808aa3a3d84d74bc64b8561dfbd2db
Source dataset
uspto-grants-1977_12
Patent number
US04064347

Reaction notes

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