Methanol → 5-(4-Nitro-phenyl)-furan-2-carboxylic acid (1-aza-bicyclo[2.2.2]oct-3-yl)-amide

HRID 2108690Notes

Reaction equation

HRID 2108690 reaction equation
Cl.Cl.[NH2:3][CH:4]1[CH:9]2[CH2:10][CH2:11][N:6]([CH2:7][CH2:8]2)[CH2:5]1.CO.C[O-].[Na+].[N+:17]([C:20]1[CH:25]=[CH:24][C:23]([C:26]2[O:30][C:29]([C:31](Cl)=[O:32])=[CH:28][CH:27]=2)=[CH:22][CH:21]=1)([O-:19])=[O:18]>ClCCl>[N:6]12[CH2:11][CH2:10][CH:9]([CH2:8][CH2:7]1)[CH:4]([NH:3][C:31]([C:29]1[O:30][C:26]([C:23]3[CH:22]=[CH:21][C:20]([N+:17]([O-:19])=[O:18])=[CH:25][CH:24]=3)=[CH:27][CH:28]=1)=[O:32])[CH2:5]2

Participants

6

Reactant 4

HCID 887MethanolHCID 197853Quinuclidine, 3-amino-, dihydrochlorideHCID 38299835-(4-nitrophenyl)furan-2-carbonyl ChlorideHCID 10942334Sodium Methoxide

Product 1

HCID 48400265-(4-Nitro-phenyl)-furan-2-carboxylic acid (1-aza-bicyclo[2.2.2]oct-3-yl)-amide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of (±)3-aminoquinuclidine dihydrochloride, methanol (250 ml), sodium methoxide (5.1 g, 95 mmol) was stirred at reflux for 1 hour. The mixture was evaporated and was mixed with methanol (150 ml) and dichloromethane (100 ml) was added and cooled on ice, and 5-(4-nitrophenyl)-2-furoyl chloride (11.2 g, 44.5 mmol), solved in dichloromethane (200 ml) was added drop-wise at 0° C. The mixture was stirred at room temperature for 21 hours. The mixture was evaporated, water (200 ml) was added and the pH was adjusted to 8.5 with triethylamine. The mixture was extracted with ethyl acetate (3×200 ml) and the pure product was isolated as free base. Yield 5.0 g (33%).

Workup

  1. temperatureat reflux for 1 hour
  2. customThe mixture was evaporated
  3. additionwas mixed with methanol (150 ml) and dichloromethane (100 ml)
  4. additionwas added
  5. additionwas added drop-wise at 0° C
  6. stirringThe mixture was stirred at room temperature for 21 hours
  7. customThe mixture was evaporated
  8. additionwater (200 ml) was added
  9. extractionThe mixture was extracted with ethyl acetate (3×200 ml)
  10. customthe pure product was isolated as free base

Sources & evidence

ORD record
ord-0f8b4a7839d343c9b4aa5ae50993071d
Source dataset
uspto-grants-2009_04
Patent number
US07514450B2

Reaction notes

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