HCID 86699742, compound → HCID 71760915, compound

HRID 515173Notes

Reaction equation

HRID 515173 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH:9][C:10](=[O:27])[C:11]2[C:16]([CH3:17])=[CH:15][C:14]([N:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)=[CH:13][C:12]=2[C:24]([CH3:26])=[CH2:25])=[CH:4][CH:3]=1>C(O)C.[Pd]>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH:9][C:10](=[O:27])[C:11]2[C:16]([CH3:17])=[CH:15][C:14]([N:18]3[CH2:19][CH2:20][O:21][CH2:22][CH2:23]3)=[CH:13][C:12]=2[CH:24]([CH3:25])[CH3:26])=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 86699742HCID 86699742, compound

Product 1

HCID 71760915HCID 71760915, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a stirred solution of N-[(4-fluorophenyl)-methyl]-2-isopropenyl-6-methyl-4-morpholin-4-yl-benzamide (0.23 g, 0.63 mmol) in ethanol (10 ml) is added 10% palladium on carbon (0.06 g). The reaction mixture is stirred under an atmosphere of hydrogen at RT for 2 h. After completion of reaction (monitored by TLC), the reaction mixture is filtered through a pad of celite, washed with ethanol and concentrated to get the crude product, which is purified by column chromatography (silica gel, 25% ethyl acetate/hexane) to afford N-[(4-fluorophenyl)-methyl]-2-isopropyl-6-methyl-4-morpholin-4-yl-benzamide (example 17) (0.16 g, 0.43 mmol, 69%). [M+H]+ 371.2.

Workup

  1. customAfter completion of reaction (monitored by TLC)
  2. filtrationthe reaction mixture is filtered through a pad of celite
  3. washwashed with ethanol
  4. concentrationconcentrated
  5. customto get the crude product, which
  6. customis purified by column chromatography (silica gel, 25% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-f067559a5df442bb9cf7f70ab634292b
Source dataset
uspto-grants-2015_08
Patent number
US09108936B2

Reaction notes

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