Hydrochloric Acid → HCID 178432626, compound

HRID 2367400Notes

Reaction equation

HRID 2367400 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([CH:13]2[O:18][CH2:17][CH2:16][N:15](CC3C=CC=CC=3)[CH2:14]2)[NH:5][C:6]=1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.Cl>[Pd].CO>[CH3:1][C:2]1[N:3]=[C:4]([CH:13]2[O:18][CH2:17][CH2:16][NH:15][CH2:14]2)[NH:5][C:6]=1[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 178432621HCID 178432621, compound

Product 1

HCID 178432626HCID 178432626, compoundYield 81.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

Palladium on carbon (0.527 g, 0.495 mmol) was added to a solution of 2-(4-methyl-5-phenyl-1H-imidazol-2-yl)-4-(phenylmethyl)morpholine (1.65 g, 4.95 mmol) and hydrochloric acid (4.12 mL, 49.5 mmol) in CH3OH (80 mL) under nitrogen, and the reaction mixture was stirred under hydrogen for 2 hours at 25° C. TLC indicated that the starting material was consumed. The mixture was filtered, washing with EtOAc (50 mL) and CH3OH (50 mL), and concentrated. Water (80 mL) was added, and the resulting mixture was lyophilized to afford the title compound (980 mg) as a brown solid. LC-MS (ES) m/z=244 [M+H]+.

Workup

  1. customwas consumed
  2. filtrationThe mixture was filtered
  3. washwashing with EtOAc (50 mL) and CH3OH (50 mL)
  4. concentrationconcentrated
  5. additionWater (80 mL) was added

Sources & evidence

ORD record
ord-419a310c54ff4147a807b62a83fb2ce9
Source dataset
uspto-grants-2014_04
Patent number
US08697685B2

Reaction notes

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