HCID 86699761, compound → HCID 72188142, compound

HRID 515196Notes

Reaction equation

HRID 515196 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH:9][C:10](=[O:27])[C:11]2[C:16]([C:17]([CH3:19])=[CH2:18])=[CH:15][C:14]([N:20]3[CH2:25][CH2:24][O:23][CH2:22][CH2:21]3)=[CH:13][C:12]=2[F:26])=[CH:4][CH:3]=1>CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH:9][C:10](=[O:27])[C:11]2[C:16]([CH:17]([CH3:19])[CH3:18])=[CH:15][C:14]([N:20]3[CH2:21][CH2:22][O:23][CH2:24][CH2:25]3)=[CH:13][C:12]=2[F:26])=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 86699761HCID 86699761, compound

Product 1

HCID 72188142HCID 72188142, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A stirred solution of N-[(4-chlorophenyl)-methyl]-2-fluoro-6-isopropenyl-4-morpholin-4-yl-benzamide (0.12 g, 0.31 mmol) in methanol (10 ml) is degassed and flushed with nitrogen before 10% palladium on carbon (25 mg) is added and the mixture is hydrogenated under hydrogen for 45 min at room temperature. After completion of the reaction (monitored by TLC), the mixture is filtered through a pad of celite and concentrated in vacuo. The resulting crude product is purified by preparative HPLC to obtain N-[(4-chlorophenyl)-methyl]-2-fluoro-6-isopropyl-4-morpholin-4-yl-benzamide (example 39) (0.04 g, 0.10 mmol, 33%). [M+H]+ 391.2.

Workup

  1. customflushed with nitrogen before 10% palladium on carbon (25 mg)
  2. additionis added
  3. customAfter completion of the reaction (monitored by TLC)
  4. filtrationthe mixture is filtered through a pad of celite
  5. concentrationconcentrated in vacuo
  6. customThe resulting crude product is purified by preparative HPLC

Sources & evidence

ORD record
ord-66b441b6a7a14207a349c2aa45462efc
Source dataset
uspto-grants-2015_08
Patent number
US09108936B2

Reaction notes

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