Hydrochloric Acid → HCID 178477902, compound

HRID 2367405Notes

Reaction equation

HRID 2367405 reaction equation
C([N:8]1[CH2:13][CH2:12][O:11][CH:10]([C:14]2[NH:18][C:17]3[CH:19]=[CH:20][C:21]([Cl:23])=[CH:22][C:16]=3[N:15]=2)[CH2:9]1)C1C=CC=CC=1.Cl.C(Cl)Cl>CO.[Pd]>[Cl:23][C:21]1[CH:20]=[CH:19][C:17]2[NH:18][C:14]([CH:10]3[O:11][CH2:12][CH2:13][NH:8][CH2:9]3)=[N:15][C:16]=2[CH:22]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 178477901HCID 178477901, compound

Product 1

HCID 178477902HCID 178477902, compoundYield 26.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 4-benzyl-2-(5-chloro-1H-benzo[d]imidazol-2-yl)morpholine (2.1 g, 6.41 mmol), and hydrogen chloride (0.234 g, 6.41 mmol) in CH3OH (50 mL) stirred under nitrogen at room temperature was added palladium on carbon (0.068 g, 0.641 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 evaporated in vacuo and the residue was dissolved in water (10 mL). The crude product was purified via reverse phase chromatography, eluting with 5˜50% of CH3OH in water, to afford the title compound (400 mg) as a white solid. LC-MS (ES) m/z=238 [M+H]+.

Workup

  1. filtrationthe mixture was filtered
  2. customThe filtrate was evaporated in vacuo
  3. dissolutionthe residue was dissolved in water (10 mL)
  4. customThe crude product was purified via reverse phase chromatography
  5. washeluting with 5˜50% of CH3OH in water

Sources & evidence

ORD record
ord-a4442be015754f2a9e56b5b92d42d7cd
Source dataset
uspto-grants-2014_04
Patent number
US08697685B2

Reaction notes

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