Hydrochloric Acid → HCID 19771932, compound

HRID 1614640Notes

Reaction equation

HRID 1614640 reaction equation
O.[ClH:2].[F:3][C:4]1[CH:5]=[C:6]([NH:11][CH:12]([C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=2)[CH:13]2[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)[CH:7]=[CH:8][C:9]=1[F:10].Br[CH2:27][C:28]1[CH:37]=[CH:36][C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH:29]=1.C(=O)(O)[O-].[Na+].Cl>C(O)C>[ClH:2].[ClH:2].[F:3][C:4]1[CH:5]=[C:6]([NH:11][CH:12]([C:19]2[CH:20]=[CH:21][C:22]([F:25])=[CH:23][CH:24]=2)[CH:13]2[CH2:18][CH2:17][N:16]([CH2:27][C:28]3[CH:37]=[CH:36][C:35]4[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=4)[CH:29]=3)[CH2:15][CH2:14]2)[CH:7]=[CH:8][C:9]=1[F:10]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 703202-BromomethylnaphthaleneHCID 516892Sodium BicarbonateHCID 19772069HCID 19772069, compound

Product 1

HCID 19771932HCID 19771932, compoundYield 76.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3.10 g (7.5 mmol) of 4-[[(3,4-difluorophenyl)amino](4-fluorophenyl)methyl]piperidine hydrochloride hydrate, 1.70 g (7.7 mmol) of 2-bromomethylnaphthalene and 5.1 g (60.7 mmol) of sodium bicarbonate in 200 mL of absolute ethanol was stirred at room temperature for 20 h. The solvent was removed in vacuo, and the residue was partitioned between methylene chloride and dilute NaOH. The organic phase was dried (Na2SO4), and the solvent was removed in vacuo. The residue was subjected to flash chromatography (silica gel, elution with 1-4% MeOH in CH2Cl2) to give an oil. This was converted to the HCl salt, and the salt was recrystallized from a mixture of methanol and diethylether to give 1.53 g (38.3%) of the title compound as a crystalline solid, mp 187°-190° C.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was partitioned between methylene chloride and dilute NaOH
  3. dry with materialThe organic phase was dried (Na2SO4)
  4. customthe solvent was removed in vacuo
  5. washThe residue was subjected to flash chromatography (silica gel, elution with 1-4% MeOH in CH2Cl2)
  6. customto give an oil
  7. customthe salt was recrystallized from a mixture of methanol and diethylether

Sources & evidence

ORD record
ord-3584ebb6d0a54a2dbd0de943bebd1bbc
Source dataset
uspto-grants-1993_03
Patent number
US05198449

Reaction notes

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