1,3-Cyclohexadiene → HCID 59784882, compound

HRID 470374Notes

Reaction equation

HRID 470374 reaction equation
[F:1][C:2]([C:11]1[CH:16]=[C:15]([N+:17]([O-])=O)[C:14]([NH2:20])=[C:13]([CH3:21])[CH:12]=1)([F:10])[CH2:3][N:4]1[CH2:9][CH2:8][O:7][CH2:6][CH2:5]1.C1CCC=CC=1>C1COCC1.[Ni]>[F:10][C:2]([C:11]1[CH:16]=[C:15]([NH2:17])[C:14]([NH2:20])=[C:13]([CH3:21])[CH:12]=1)([F:1])[CH2:3][N:4]1[CH2:5][CH2:6][O:7][CH2:8][CH2:9]1

Participants

5

Reactant 2

HCID 116051,3-CyclohexadieneHCID 59784467HCID 59784467, compound

Product 1

HCID 59784882HCID 59784882, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(1,1-difluoro-2-morpholin-4-yl-ethyl)-2-methyl-6-nitro-phenylamine (60 mg, 0.2 mmol) in THF (5 mL) was added Raney nickel (100 mg) and cyclohexadiene (0.5 mL). TLC indicated the formation of the product after the reaction mixture was stirred for 3.5 h). The reaction mixture was filtered over Celite and evaporated to afforded crude title product that was used for the next step reaction without purification.

Workup

  1. filtrationThe reaction mixture was filtered over Celite
  2. customevaporated

Sources & evidence

ORD record
ord-7fe4feb81dae4172b8552c8d82b45d8a
Source dataset
uspto-grants-2014_01
Patent number
US08629147B2

Reaction notes

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