Hydrochloric Acid → HCID 178489844, compound

HRID 2367385Notes

Reaction equation

HRID 2367385 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2[N:10]=[C:11]([CH:14]3[O:19][CH2:18][CH2:17][N:16](CC4C=CC=CC=4)[CH2:15]3)[NH:12][CH:13]=2)[CH:6]=[CH:7][CH:8]=1.Cl>[Pd].CO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2[N:10]=[C:11]([CH:14]3[O:19][CH2:18][CH2:17][NH:16][CH2:15]3)[NH:12][CH:13]=2)[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 178489843HCID 178489843, compound

Product 1

HCID 178489844HCID 178489844, compoundYield 168.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Palladium on carbon (10 wt %, 0.609 g, 0.572 mmol) was added to a solution of 2-{-4-[3-(methyloxy)phenyl]-1H-imidazol-2-yl}-4-(phenylmethyl)morpholine (2.0 g, 5.72 mmol) and hydrochloric acid (4.76 mL, 57.2 mmol) in CH3OH (80 mL) under nitrogen, and the resulting mixture was stirred under hydrogen overnight at room temperature. The mixture was filtered, washing with CH2Cl2 (50 mL) and CH3OH (3×50 mL), and then concentrated. Water (80 mL) was added, and the resulting mixture was lyophilized to afford an HCL salt of the title compound (2.5 g) as a brown oil. LC-MS (ES) m/z=260 [M+H]+.

Workup

  1. filtrationThe mixture was filtered
  2. washwashing with CH2Cl2 (50 mL) and CH3OH (3×50 mL)
  3. concentrationconcentrated
  4. additionWater (80 mL) was added

Sources & evidence

ORD record
ord-3234d24afb4247529ce90d2d3ccfb174
Source dataset
uspto-grants-2014_04
Patent number
US08697685B2

Reaction notes

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