1-(2-fluoroethyl)-N-(3-methoxy-4-nitrophenyl)azetidin-3-amine → HCID 86709973, compound

HRID 574276Notes

Reaction equation

HRID 574276 reaction equation
[F:1][CH2:2][CH2:3][N:4]1[CH2:7][CH:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[C:11]([O:18][CH3:19])[CH:10]=2)[CH2:5]1>O1CCOCC1.[Pd]>[F:1][CH2:2][CH2:3][N:4]1[CH2:7][CH:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([NH2:15])=[C:11]([O:18][CH3:19])[CH:10]=2)[CH2:5]1

Participants

4

Reactant 1

HCID 867099741-(2-fluoroethyl)-N-(3-methoxy-4-nitrophenyl)azetidin-3-amine

Product 1

HCID 86709973HCID 86709973, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

A solution of 1-(2-fluoroethyl)-N-(3-methoxy-4-nitrophenyl)azetidin-3-amine (2.6 g) and Pd/C (1 g) in 1,4-dioxane (50 mL) was hydrogenated for 4 hours at room temperature. The reaction mixture was filtered through diatomaceous earth, washing with MeOH. The filtrate was concentrated and purified by column chromatography (DCM/MeOH=50/1 as elution) to provide the title compound (1.57 g, yield 68%, M+H+=240.2).

Workup

  1. filtrationThe reaction mixture was filtered through diatomaceous earth
  2. washwashing with MeOH
  3. concentrationThe filtrate was concentrated
  4. custompurified by column chromatography (DCM/MeOH=50/1 as elution)

Sources & evidence

ORD record
ord-047b79473a814793a472cf1f95305f7d
Source dataset
uspto-grants-2015_05
Patent number
US09034885B2

Reaction notes

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