Hydrochloric Acid → N-(2-fluoro-4-chloro-5-cyclopentyloxyphenyl)-N'-(2-bromoethyl)-3,4,5,6-tetrahydrophthalamide

HRID 1720417Notes

Reaction equation

HRID 1720417 reaction equation
Br.[NH2:2][CH2:3][CH2:4][Br:5].[C:6](=O)([O-])[O-:7].[K+].[K+].[F:12][C:13]1[CH:18]=[C:17]([Cl:19])[C:16]([O:20][CH:21]2[CH2:25][CH2:24][CH2:23][CH2:22]2)=[CH:15][C:14]=1[N:26]1C(=O)[CH:30]2[CH2:33][CH2:34][CH2:35][C:28](=[CH:29]2)[C:27]1=[O:36].Cl>C(#N)C>[F:12][C:13]1[CH:18]=[C:17]([Cl:19])[C:16]([O:20][CH:21]2[CH2:22][CH2:23][CH2:24][CH2:25]2)=[CH:15][C:14]=1[NH:26][C:27](=[O:36])[C:28]1[CH2:35][CH2:34][CH2:33][CH2:30][C:29]=1[C:6]([NH:2][CH2:3][CH2:4][Br:5])=[O:7]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 27742172-Bromoethylamine hydrobromideHCID 19425191N-(2-fluoro-4-chloro-5-cyclopentyloxyphenyl)-3,4,5,6-tetrahydroisophthalimide

Product 1

HCID 19425254N-(2-fluoro-4-chloro-5-cyclopentyloxyphenyl)-N'-(2-bromoethyl)-3,4,5,6-tetrahydrophthalamideYield 165.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-Aminoethyl bromide hydrobromide (0.280 g, 1.37 mmol) and potassium carbonate (0.110 g, 0.796 mmol) were placed into a round bottom flask (25 cc), followed by stirring at room temperature in an acetonitrile solvent until the generation of gas ceased. Then, N-(2-fluoro-4-chloro-5-cyclopentyloxyphenyl)-3,4,5,6-tetrahydroisophthalimide (0.500 g, 1.37 mmol) was added thereto, followed by stirring for 30 minutes at room temperature. After completion of the reaction, the reaction mixture was poured into 1N hydrochloric acid (20 ml), and the mixture was extracted with ethyl acetate (30 ml x 3 portions). After drying the organic layer over anhydrous magnesium sulfate, the drying agent was removed, and the solvent was distilled off under reduced pressure. The precipitated crystals were isolated by filtration, washed with hexane and dried to obtain N-(2-fluoro-4-chloro-5-cyclopentyloxyphenyl)-N'-(2-bromoethyl)-3,4,5,6-tetrahydrophthalamide as white crystals (0.644 g, 96.4% yield).

Workup

  1. customAfter completion of the reaction
  2. extractionthe mixture was extracted with ethyl acetate (30 ml x 3 portions)
  3. dry with materialAfter drying the organic layer over anhydrous magnesium sulfate
  4. customthe drying agent was removed
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe precipitated crystals were isolated by filtration
  7. washwashed with hexane
  8. customdried

Sources & evidence

ORD record
ord-525d6d1a8f5e4dac9f0d472fe391cd03
Source dataset
uspto-grants-1996_04
Patent number
US05506190

Reaction notes

Loading…