Sodium Hydroxide → N-(3-Bromo-4-fluorobenzyl)tetrahydro-2H-thiopyran-4-amine

HRID 467956Notes

Reaction equation

HRID 467956 reaction equation
[S:1]1[CH2:6][CH2:5][C:4](=O)[CH2:3][CH2:2]1.[Br:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][C:16]=1[F:17])[CH2:12][NH2:13].[OH-].[Na+]>C(Cl)(Cl)Cl>[Br:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][C:16]=1[F:17])[CH2:12][NH:13][CH:4]1[CH2:5][CH2:6][S:1][CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 66173Tetrahydrothiopyran-4-oneHCID 2724902(3-Bromo-4-fluorophenyl)methanamine

Product 1

HCID 58049393N-(3-Bromo-4-fluorobenzyl)tetrahydro-2H-thiopyran-4-amineYield 56.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of tetrahydro-4H-thiopyran-4-one (1.16 g) in chloroform (50 mL), 3-bromo-4-fluorobenzylamine (2.41 g) was added and the resulting mixture was stirred at room temperature for an hour. Sodium (triacetoxy)borohyride (6.36 g) was added and the resulting mixture was stirred overnight. To the reaction mixture, an aqueous solution of 2 M sodium hydroxide was added and after stirring the resulting mixture, extraction was performed with chloroform. The chloroform layer was dried over anhydrous sodium sulfate. After filtering off the desiccant, the solvent was distilled off under reduced pressure and the resulting residue was purified by column chromatography (silica gel cartridge; chloroform/methanol=100:0 to 99:1) to give the titled compound (1.72 g).

Workup

  1. stirringthe resulting mixture was stirred overnight
  2. stirringafter stirring
  3. extractionthe resulting mixture, extraction
  4. dry with materialThe chloroform layer was dried over anhydrous sodium sulfate
  5. filtrationAfter filtering off the desiccant
  6. distillationthe solvent was distilled off under reduced pressure
  7. customthe resulting residue was purified by column chromatography (silica gel cartridge; chloroform/methanol=100:0 to 99:1)

Sources & evidence

ORD record
ord-bd8be51e2f334f0eb12480e4c0d594ad
Source dataset
uspto-grants-2014_01
Patent number
US08623898B2

Reaction notes

Loading…