3-Fluoroaniline → HCID 178523760, compound

HRID 1914647Notes

Reaction equation

HRID 1914647 reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][C:3]=1[C:4]([NH:6][C@H:7]1[CH2:12][CH2:11][C@H:10]([CH:13]=O)[CH2:9][CH2:8]1)=[O:5].[F:23][C:24]1[CH:25]=[C:26]([CH:28]=[CH:29][CH:30]=1)[NH2:27].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+]>C(Cl)Cl>[Cl:1][C:2]1[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][C:3]=1[C:4]([NH:6][C@H:7]1[CH2:12][CH2:11][C@H:10]([CH2:13][NH:27][C:26]2[CH:28]=[CH:29][CH:30]=[C:24]([F:23])[CH:25]=2)[CH2:9][CH2:8]1)=[O:5]

Participants

6

Reactant 4

HCID 97423-FluoroanilineHCID 14798Sodium HydroxideHCID 5049666Sodium triacetoxyborohydrideHCID 178520978HCID 178520978, compound

Product 1

HCID 178523760HCID 178523760, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a 50 mL round-bottomed flask containing trans-2-chloro-N-(4-formyl-cyclohexyl)-5-trifluoromethyl-benzamide (Ex. 1 step 3) (1.0 g, 3.0 mmol) and 3-fluoroaniline (0.29 mL, 3.0 mmol) in dry DCM (25 mL) is added sodium triacetoxyborohydride (953 mg, 4.49 mmol) in three portions over 1-2 minutes. The suspension is stirred at RT for 1 hour. 1N sodium hydroxide (25 mL) is added and the mixture is stirred at RT for 20 min. The mixture is then diluted with DCM (50 mL) and the DCM layer separated and washed with 1M HCl (25 mL) and brine (15 mL), dried (MgSO4), filtered and evaporated to give a colourless solid. The crude product is redissolved in DCM, absorbed directly onto silica gel and columned on silica gel using a 50 g pre-packed column and eluted with 30% EtOAc/isohexane. Product is isolated as a colourless oil which is triturated with diether ether-isohexane to afford the title compound as colourless crystals. [MH+429.24].

Workup

  1. stirringthe mixture is stirred at RT for 20 min
  2. customthe DCM layer separated
  3. washwashed with 1M HCl (25 mL) and brine (15 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. customto give a colourless solid
  8. customabsorbed directly onto silica gel
  9. washeluted with 30% EtOAc/isohexane
  10. customProduct is isolated as a colourless oil which
  11. customis triturated with diether ether-isohexane

Sources & evidence

ORD record
ord-82cbec0e1a6a4510b80096e40fd1281c
Source dataset
uspto-grants-2013_12
Patent number
US08614213B2

Reaction notes

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