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

HRID 1076913Notes

Reaction equation

HRID 1076913 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 was added 9.8 g (0.033 mole) of sodium dichromate over 1/2 hour. The mixture was 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 was 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 desired product. M.P. 93°-95°C.

Workup

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

Sources & evidence

ORD record
ord-093c0360adfe40a9b4de6a32769d41b2
Source dataset
uspto-grants-1976_05
Patent number
US03957989

Reaction notes

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