Sodium hydride → HCID 21245854, compound

HRID 620286Notes

Reaction equation

HRID 620286 reaction equation
[NH2:1][C:2]1[C:18]([Cl:19])=[CH:17][C:5]([C:6]([NH:8][CH:9]2[CH:14]3[CH2:15][CH2:16][N:11]([CH2:12][CH2:13]3)[CH2:10]2)=[O:7])=[C:4](O)[CH:3]=1.[H-].[Na+]>>[CH2:6]([O:7][C:5]1([CH:17]=[C:18]([Cl:19])[C:2]([NH2:1])=[CH:3][CH2:4]1)[C:6]([NH:8][CH:9]1[CH:14]2[CH2:15][CH2:16][N:11]([CH2:12][CH2:13]2)[CH2:10]1)=[O:7])[CH:5]=[CH2:4]

Participants

3

Reactant 2

HCID 24758Sodium hydrideHCID 156708204-Amino-N-(1-azabicyclo[2.2.2]octan-3-yl)-5-chloro-2-hydroxybenzamide

Product 1

HCID 21245854HCID 21245854, compoundYield 90.7%

Procedure

4-Amino-N-(1-azabicyclo[2.2.2]oct-3-yl)-5-chloro-2-hydroxybenzamide (444 mg) was added to a suspension of sodium hydride (66 mg of a 60% oil emulsion, washed with pentane) in DMF (10 mL). When the evolution of hydrogen ceased, the solution was treated with allyl bromide (195 mg) for 1 hour. The solution was diluted with ethyl acetate and the volume of solvent mixture consisting of acetonitrile, methanol and ammonium hydroxide in the ratio of 100:15:0.5, and flash chromatographed over silica gel eluting with the same solvent system. The appropriate fractions were combined and concentrated. The solid obtained was collected by filtration and dried under vacuum to yield 0.230 g (46%) of the title compound, m.p. 220° C.

Workup

  1. washwashed with pentane) in DMF (10 mL)
  2. additionthe solution was treated with allyl bromide (195 mg) for 1 hour
  3. additionThe solution was diluted with ethyl acetate
  4. customchromatographed over silica gel eluting with the same solvent system
  5. concentrationconcentrated
  6. customThe solid obtained
  7. filtrationwas collected by filtration
  8. customdried under vacuum

Sources & evidence

ORD record
ord-0a32fc56eae24ade989f624bf00a7241
Source dataset
uspto-grants-1989_04
Patent number
US04820715

Reaction notes

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