4-[2-(4-Fluoro-phenyl)-cyclohex-1-enyl]-pyridin-2-ylamine → 4-[cis-2-(4-Fluoro-phenyl)-cyclohexyl]-pyridin-2-ylamine

HRID 1023473Notes

Reaction equation

HRID 1023473 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:13][CH2:12][CH2:11][CH2:10][C:9]=2[C:14]2[CH:19]=[CH:18][N:17]=[C:16]([NH2:20])[CH:15]=2)=[CH:4][CH:3]=1.[H][H]>CO.[Pd]>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C@H:8]2[CH2:13][CH2:12][CH2:11][CH2:10][C@H:9]2[C:14]2[CH:19]=[CH:18][N:17]=[C:16]([NH2:20])[CH:15]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 690855804-[2-(4-Fluoro-phenyl)-cyclohex-1-enyl]-pyridin-2-ylamineHCID 178418361HCID 178418361, compound

Product 1

HCID 690841454-[cis-2-(4-Fluoro-phenyl)-cyclohexyl]-pyridin-2-ylamineYield 54.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 4-[2-(4-Fluoro-phenyl)-cyclohex-1-enyl]-pyridin-2-ylamine (220 mg, 0.82 mmol, synthesis described in example 56) in methanol (10 mL) is passed through H-Cube® Continuous-flow Hydrogenation Reactor at 60° C. and under 60 psi hydrogen pressure. The 10% Pd/C cartridge is used and the reaction is run for 48 hours. The solvent is removed to give 120 mg of the desired product.

Workup

  1. customThe solvent is removed

Sources & evidence

ORD record
ord-3e7c8eb1a2fa41b0ab68a1f44c4c4fcd
Source dataset
uspto-grants-2014_05
Patent number
US08722709B2

Reaction notes

Loading…