4-(5-Bromo-3-methyl-2-pyridinyl)butylamine → HCID 178422459, compound

HRID 1252540Notes

Reaction equation

HRID 1252540 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH3:13])[C:5]([CH2:8][CH2:9][CH2:10][CH2:11][NH2:12])=[N:6][CH:7]=1.Cl[C:15]1[C:19]2[CH:20]=[CH:21][C:22]([N+:24]([O-:26])=[O:25])=[CH:23][C:18]=2[S:17](=[O:28])(=[O:27])[N:16]=1>C(#N)C>[Br:1][C:2]1[CH:3]=[C:4]([CH3:13])[C:5]([CH2:8][CH2:9][CH2:10][CH2:11][NH:12][C:15]2[C:19]3[CH:20]=[CH:21][C:22]([N+:24]([O-:26])=[O:25])=[CH:23][C:18]=3[S:17](=[O:27])(=[O:28])[N:16]=2)=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 130942724-(5-Bromo-3-methyl-2-pyridinyl)butylamineHCID 1415429627605-74-9

Product 1

HCID 178422459HCID 178422459, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 4-(5-bromo-3-methyl-2-pyridinyl)butylamine (318 mg, 1.31 mmol) and 3-chloro-6-nitrobenzisothiazole 1,1-dioxide (U.S. Pat. No. 4,490,527) (357 mg, 1.45 mmol) in 15 ml acetonitrile was stirred under dry nitrogen at room temperature then heated to reflux for several minutes until the material dissolved. The solvent was removed under reduced pressure and the residue recrystallized from ethanol and triturated with hot ethanol, yielding 250 mg (39%) of the title compound as the hydrochloride salt, m.p. 235°-242° C. IR(KBr) 1620, 1345, 1300, 1160 cm-1.

Workup

  1. temperaturethen heated
  2. temperatureto reflux for several minutes until the material
  3. dissolutiondissolved
  4. customThe solvent was removed under reduced pressure
  5. customthe residue recrystallized from ethanol
  6. customtriturated with hot ethanol

Sources & evidence

ORD record
ord-3e38d86c68a44e72ac748a1456dbcf30
Source dataset
uspto-grants-1988_05
Patent number
US04743692

Reaction notes

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