Hydrochloric Acid → HCID 178505466, compound

HRID 2367410Notes

Reaction equation

HRID 2367410 reaction equation
[F:1][C:2]1[CH:23]=[CH:22][C:5]2[NH:6][C:7]([CH:9]3[O:14][CH2:13][CH2:12][N:11](CC4C=CC=CC=4)[CH2:10]3)=[N:8][C:4]=2[CH:3]=1.Cl.C(Cl)Cl>CO.[Pd]>[F:1][C:2]1[CH:23]=[CH:22][C:5]2[NH:6][C:7]([CH:9]3[O:14][CH2:13][CH2:12][NH:11][CH2:10]3)=[N:8][C:4]=2[CH:3]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 178505465HCID 178505465, compound

Product 1

HCID 178505466HCID 178505466, compoundYield 93.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 5-fluoro-2-[4-(phenylmethyl)-2-morpholinyl]-1H-benzimidazole (3.0 g, 9.64 mmol), and hydrogen chloride (0.703 g, 19.27 mmol) in CH3OH (50 mL) stirred under nitrogen at room temperature was added palladium on carbon (0.103 g, 0.964 mmol), and the reaction mixture was stirred under hydrogen at 25° C. overnight. CH2Cl2 was added and the mixture was filtered. The filtrate was concentrated in vacuo and the residue was triturated with EtOAc, filtered and dried to afford a hydrochloride salt of the title compound as a off-white solid (2.0 g). LC-MS (ES) m/z=222 [M+H]+.

Workup

  1. filtrationthe mixture was filtered
  2. concentrationThe filtrate was concentrated in vacuo
  3. customthe residue was triturated with EtOAc
  4. filtrationfiltered
  5. customdried

Sources & evidence

ORD record
ord-09336d3b15b34bada0d3c1da6c687086
Source dataset
uspto-grants-2014_04
Patent number
US08697685B2

Reaction notes

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