Sodium Dichromate → 2,7-Bis(4-piperidinobutyryl)xanthone

HRID 1578659Notes

Reaction equation

HRID 1578659 reaction equation
[N:1]1([CH2:7][CH2:8][CH2:9][C:10]([C:12]2[CH:25]=[CH:24][C:23]3[O:22][C:21]4[C:16](=[CH:17][C:18]([C:26](=[O:36])[CH2:27][CH2:28][CH2:29][N:30]5[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]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:38].[Na+].[Na+]>C(O)(=O)C>[N:1]1([CH2:7][CH2:8][CH2:9][C:10]([C:12]2[CH:25]=[CH:24][C:23]3[O:22][C:21]4[C:16](=[CH:17][C:18]([C:26](=[O:36])[CH2:27][CH2:28][CH2:29][N:30]5[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35]5)=[CH:19][CH:20]=4)[C:15](=[O:38])[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 5154014-(1-piperidyl)-1-[7-[4-(1-piperidyl)butanoyl]-9H-xanthen-2-yl]butan-1-one

Product 1

HCID 5153952,7-Bis(4-piperidinobutyryl)xanthone

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 9.8 g (0.025 mole) of 2,7-bis(4-piperidinobutyryl)xanthene in 300 ml of glacial acetic acid is added 9.8 g (0.033 mole) of sodium dichromate over 1/2 hour. The mixture is stirred for 11/2 hours, refluxed for 1 hour, then evaporated to near dryness, cooled, diluted with water and made alkaline with 28% NH4OH solution. The resulting solid is extracted with methylene chloride, chromatographed on alumina using methylene chloride as the eluant, recrystallized from heptane and dried under vacuum at 60°C to give the title compound, M.P. 93°-95°C.

Workup

  1. temperaturerefluxed for 1 hour
  2. customevaporated
  3. temperaturecooled
  4. additiondiluted with water
  5. extractionThe resulting solid is extracted with methylene chloride
  6. customchromatographed on alumina
  7. customrecrystallized from heptane
  8. customdried under vacuum at 60°C

Sources & evidence

ORD record
ord-3039d4e0fb8b43049dd75c08a7942116
Source dataset
uspto-grants-1976_02
Patent number
US03937833

Reaction notes

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