(S)-quinuclidin-3-amine → HCID 19743266, compound

HRID 2254842Notes

Reaction equation

HRID 2254842 reaction equation
[NH2:1][C@H:2]1[CH:7]2[CH2:8][CH2:9][N:4]([CH2:5][CH2:6]2)[CH2:3]1.[C:10]([NH:13][C:14]1[C:22]([Cl:23])=[CH:21][C:17]([C:18]([Cl:20])=[O:19])=[C:16]([O:24][CH3:25])[CH:15]=1)(=[O:12])[CH3:11]>[OH-].[Na+].O1CCOCC1>[ClH:20].[N:4]12[CH2:9][CH2:8][CH:7]([CH2:6][CH2:5]1)[CH:2]([NH:1][C:18](=[O:19])[C:17]1[CH:21]=[C:22]([Cl:23])[C:14]([NH:13][C:10](=[O:12])[CH3:11])=[CH:15][C:16]=1[O:24][CH3:25])[CH2:3]2

Participants

5

Reactant 2

HCID 719216(S)-quinuclidin-3-amineHCID 113799924-Acetamido-5-chloro-2-methoxybenzoyl chloride

Product 1

HCID 19743266HCID 19743266, compound

Reagents, catalysts & solvents 2

HCID 14798Sodium HydroxideSolventHCID 312751,4-DioxaneSolvent

Procedure

(S)-(-)-3-Aminoquinuclidine (1.9 g) is dissolved in 33.5 ml of 1N aqueous sodium hydroxide solution. 4-Acetamido-5-chloro-2-methoxybenzoyl chloride (3.75 g) dissolved in 70 ml of dioxane is added dropwise to this solution. After 15 minutes' stirring, the medium is acidified, washed with chloroform and alkalinized with concentrated aqueous sodium hydroxide solution, and the product extracted with chloroform. The organic phase is dried (over Na2SO4) and then evaporated. The oily residue is dissolved in ethanol and ethanolic hydrogen chloride is added until an acid pH is obtained. The N-(3-quinuclidinyl)-4-acetamido-5-chloro-2-methoxybenzamide hydrochloride thereby formed precipitates (quantitative yield), and the latter is collected by filtration.

Workup

  1. additionis added dropwise to this solution
  2. washwashed with chloroform
  3. extractionthe product extracted with chloroform
  4. dry with materialThe organic phase is dried (over Na2SO4)
  5. customevaporated
  6. dissolutionThe oily residue is dissolved in ethanol
  7. additionethanolic hydrogen chloride is added until an acid pH
  8. customis obtained

Sources & evidence

ORD record
ord-8bb926a7a76a420e832e1ec3d428a577
Source dataset
uspto-grants-1993_08
Patent number
US05237066

Reaction notes

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