Hydrochloric Acid → HCID 178488061, compound

HRID 2367390Notes

Reaction equation

HRID 2367390 reaction equation
[CH3:1][O:2][C:3]1[CH:24]=[CH:23][C:6]2[NH:7][C:8]([CH:10]3[O:15][CH2:14][CH2:13][N:12](CC4C=CC=CC=4)[CH2:11]3)=[N:9][C:5]=2[CH:4]=1.Cl.C(Cl)Cl>CO.[Pd]>[CH3:1][O:2][C:3]1[CH:24]=[CH:23][C:6]2[NH:7][C:8]([CH:10]3[O:15][CH2:14][CH2:13][NH:12][CH2:11]3)=[N:9][C:5]=2[CH:4]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 178488060HCID 178488060, compound

Product 1

HCID 178488061HCID 178488061, compoundYield 34.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 5-(methyloxy)-2-[4-(phenylmethyl)-2-morpholinyl]-1H-benzimidazole (2.0 g, 6.18 mmol), and hydrogen chloride (0.451 g, 12.37 mmol) in CH3OH (50 mL) stirred under nitrogen at room temperature was added palladium on carbon (0.066 g, 0.618 mmol). The reaction mixture was stirred under hydrogen at 25° C. for 3 hours. CH2Cl2 was added and the mixture was filtered. The filtrate was concentrated in vacuo. The crude product was added to a silica gel column and was eluted with 90:10 CH2Cl2/CH3OH to afford the title compound (500 mg). LC-MS (ES) m/z=234 [M+H]+.

Workup

  1. filtrationthe mixture was filtered
  2. concentrationThe filtrate was concentrated in vacuo
  3. additionThe crude product was added to a silica gel column
  4. washwas eluted with 90:10 CH2Cl2/CH3OH

Sources & evidence

ORD record
ord-9f129ccb6d614e3ca2b446a20dcf5d8a
Source dataset
uspto-grants-2014_04
Patent number
US08697685B2

Reaction notes

Loading…