Potassium Carbonate → HCID 23044933, compound

HRID 2352487Notes

Reaction equation

HRID 2352487 reaction equation
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[CH:3]([NH:9][C:10](=[O:23])[C:11]1[CH:16]=[C:15]([Cl:17])[C:14]([NH:18][C:19](=[O:21])[CH3:20])=[CH:13][C:12]=1[OH:22])[CH2:2]2.C(=O)([O-])[O-].[K+].[K+].Br[CH2:31][CH:32]1[CH2:34][CH2:33]1>C(C(C)=O)C(C)C>[N:1]12[CH2:6][CH2:5][CH:4]([CH2:7][CH2:8]1)[CH:3]([NH:9][C:10](=[O:23])[C:11]1[CH:16]=[C:15]([Cl:17])[C:14]([NH:18][C:19](=[O:21])[CH3:20])=[CH:13][C:12]=1[O:22][CH2:31][CH:32]1[CH2:34][CH2:33]1)[CH2:2]2

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 81503BromomethylcyclopropaneHCID 23044932HCID 23044932, compound

Product 1

HCID 23044933HCID 23044933, compoundYield 84.2%

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

A suspension of N-(1-azabicyclo[2.2.2]oct-3-yl)-2-hydroxy-4-acetamido-5-chlorobenzamide (6.75 g; 0.02 moles) (m.p. of hydrochloride 315°-317° C. (d)), potassium carbonate (2.76 g; 0.02 moles), 91.5% bromomethylcyclopropane (3.54 g; 0.024 moles) and methyl isobutyl ketone (40 ml) was boiled under reflux for 48 hours. After cooling, the reaction mixture was washed with water, 1N sodium hydroxide aqueous solution and again with water. The organic solution was dried (Na2SO4), decolorized with charcoal and the solvent removed in vacuo to give crude N-(1-azabicyclo[2.2.2]oct-3-yl)-2-cyclopropylmethoxy-4-acetamido-5-chlorobenzamide (6.6 g) as an oil, which was crystallized from acetonitrile, m.p. 211°-213° C. (d).

Workup

  1. temperatureunder reflux for 48 hours
  2. temperatureAfter cooling
  3. washthe reaction mixture was washed with water, 1N sodium hydroxide aqueous solution and again with water
  4. dry with materialThe organic solution was dried (Na2SO4)
  5. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-fe7bc59ce22244e1b4e011c84baa1c33
Source dataset
uspto-grants-1989_10
Patent number
US04877780

Reaction notes

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