Water → HCID 2732918, compound

HRID 1780794Notes

Reaction equation

HRID 1780794 reaction equation
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[C:3](=[O:9])[CH2:2]2.[Cl:10][C:11]1[CH:18]=[CH:17][C:14]([CH:15]=O)=[CH:13][CH:12]=1.[OH-].[Na+].O>C(O)C>[Cl:10][C:11]1[CH:18]=[CH:17][C:14]([CH:15]=[C:2]2[C:3](=[O:9])[CH:4]3[CH2:7][CH2:8][N:1]2[CH2:6][CH2:5]3)=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 962WaterHCID 77264-ChlorobenzaldehydeHCID 14798Sodium HydroxideHCID 195073-Quinuclidinone

Product 1

HCID 2732918HCID 2732918, compoundYield 79.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 3-quinuclidinone (54.5 g), 4-chlorobenzaldehyde (84.0 g) and sodium hydroxide (3.50 g) in absolute ethanol (400 cm3) was heated at reflux for 2.5 hours. The mixture was cooled and addition of water (100 cm3) caused the product to precipitate as an orange solid. The precipitate was collected and washed with 1:1 ethanol-water (400 cm3). The mother-liquors were stood for 2 days, after which time further precipitated material was collected. The orange solid was redissolved in dichloromethane (800 cm3) and washed with water (200 cm3). The organic phase was dried (MgSO4), filtered and evaporated to dryness to give the title compound as a bright yellow powder (86.2 g, 76%), mp. 108°-110° C.; δH (360 MHz; CDCl3) 1.99-2.05 (4H, m, 2×NCH2CH2), 2.63 [(1H, quintet, J=2.9, (CH2)2CH], 2.92-3.01 (2H, m, 2×NCH), 3.11-3.19 (2H, m, 2×NCH), 6.95 (1H, s, C=CH), 7.33 (2H, d, J=8.6, 2×ArH o to Cl) and 7.98 (2H, d, J=8.6, 2×ArH m to Cl); m/z (CI+ ; NH3) 248 (M+ +H, 100%).

Workup

  1. temperatureat reflux for 2.5 hours
  2. temperatureThe mixture was cooled
  3. customto precipitate as an orange solid
  4. customThe precipitate was collected
  5. washwashed with 1:1 ethanol-water (400 cm3)
  6. customafter which time further precipitated material was collected
  7. dissolutionThe orange solid was redissolved in dichloromethane (800 cm3)
  8. washwashed with water (200 cm3)
  9. dry with materialThe organic phase was dried (MgSO4)
  10. filtrationfiltered
  11. customevaporated to dryness

Sources & evidence

ORD record
ord-7820dc9305b04fb08a858045efcb9faa
Source dataset
uspto-grants-1997_05
Patent number
US05631269

Reaction notes

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