Acetone → HCID 13189033, compound

HRID 1995303Notes

Reaction equation

HRID 1995303 reaction equation
Br.Br.[CH:3]12[CH2:11][CH2:10][CH:7]([CH2:8][CH2:9]1)[CH2:6][N:5]([CH2:12][CH2:13][N:14]1[CH2:19][CH2:18][C:17]3[C:20]4[CH:28]=[C:27]([OH:29])[C:26]([OH:30])=[CH:25][C:21]=4[O:22][C:23](=[O:24])[C:16]=3[CH2:15]1)[CH2:4]2.C(=O)([O-])[O-].[K+].[K+].S(OCC)(O[CH2:41][CH3:42])(=O)=O.[CH3:46][C:47](C)=O>>[CH:3]12[CH2:11][CH2:10][CH:7]([CH2:8][CH2:9]1)[CH2:6][N:5]([CH2:12][CH2:13][N:14]1[CH2:19][CH2:18][C:17]3[C:20]4[CH:28]=[C:27]([O:29][CH2:41][CH3:42])[C:26]([O:30][CH2:46][CH3:47])=[CH:25][C:21]=4[O:22][C:23](=[O:24])[C:16]=3[CH2:15]1)[CH2:4]2

Participants

5

Reactant 4

HCID 180AcetoneHCID 6163Diethyl Sulfate2×HCID 11430Potassium CarbonateHCID 13189032HCID 13189032, compound

Product 1

HCID 13189033HCID 13189033, compound

Procedure

A mixture 3-[2-(3-azabicyclo-[3.2.2]non-3-yl)ethyl]-1,2,3,4-tetrahydro-8,9-dihydroxy-5H-[1]benzopyrano[3,4-c]pyridin-5-one dihydrobromide (11.5 g, 0.020 moles), potassium carbonate (15.0 g, 0.11 moles), and diethyl sulfate (10.4 g, 0.067 moles) in 2.5 l of acetone is stirred at reflux for 21 hours. Additional diethyl sulfate (59 g, 0.38 moles) is added, and the mixture is heated for an additional 30 hours. The cooled mixture is filtered, and the filter cake is digested twice in hot acetone (500 ml) and refiltered. The combined filtrates are evaporated, and the residue is distributed between dichloromethane (1500 ml) and water (750 ml). The organic layer is separated, washed four times with 2.5% aqueous sodium hydroxide (750 ml), dried over sodium sulfate, and evaporated. The crude product was recrystallized twice as the free base from acetonitrile to yield the final product (5.4 g), mp 132°-134° C.

Workup

  1. temperatureat reflux for 21 hours
  2. temperaturethe mixture is heated for an additional 30 hours
  3. filtrationThe cooled mixture is filtered
  4. customThe combined filtrates are evaporated
  5. customThe organic layer is separated
  6. washwashed four times with 2.5% aqueous sodium hydroxide (750 ml)
  7. dry with materialdried over sodium sulfate
  8. customevaporated
  9. customThe crude product was recrystallized twice as the free base from acetonitrile

Sources & evidence

ORD record
ord-c01dbdba4be040ea956bfd36f3b93b02
Source dataset
uspto-grants-1983_09
Patent number
US04404138

Reaction notes

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