Potassium Carbonate → HCID 23044933, compound

HRID 2107942Notes

Reaction equation

HRID 2107942 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-311e8f5fefe74cffbebeb9f6978aadfc
Source dataset
uspto-grants-1990_06
Patent number
US04937236

Reaction notes

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