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

HRID 1578653Notes

Reaction equation

HRID 1578653 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 9.0 g (0.019 mole) 2,7-bis(4-piperidinobutyryl)fluorene, 7.54 g (0.0253 mole) sodium dichromate and 300 ml of glacial acetic acid is stirred and refluxed for 1 hour. The reaction mixture is evaporated to semi-dryness and made basic using concentrated ammonium hydroxide. The solid which precipitates is filtered, washed with water and chromatographed on alumina using chloroform as the eluant. The solvent is removed from the fraction collected, leaving a solid residue which is recrystallized three times from chloroform-acetone to yield 2,7-bis(4-piperidinobutyryl)fluoren-9-one, M.P. 168°-170°C.

Workup

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

Sources & evidence

ORD record
ord-9ee0872a30df4be8ac37f6f6e29b5190
Source dataset
uspto-grants-1976_02
Patent number
US03937833

Reaction notes

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