Hydrochloric Acid → (S)-3-Methoxy-5-(2-methylpyrrolidin-1-YL)aniline

HRID 1410109

Reaction equation

HRID 1410109 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([N:12]2[CH2:16][CH2:15][CH2:14][C@@H:13]2[CH3:17])[CH:6]=[C:7]([N+:9]([O-])=O)[CH:8]=1.Cl>O1CCOCC1.O.[Zn]>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([NH2:9])[CH:6]=[C:5]([N:12]2[CH2:16][CH2:15][CH2:14][C@@H:13]2[CH3:17])[CH:4]=1

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 68379376(S)-1-(3-methoxy-5-nitrophenyl)-2-methylpyrrolidine

Product 1

HCID 68379440(S)-3-Methoxy-5-(2-methylpyrrolidin-1-YL)anilineYield 72%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a suspension of (S)-1-(3-methoxy-5-nitrophenyl)-2-methylpyrrolidine (430 mg, 1.82 mmol) and Zinc (1.18 g, 18.2 mmol) in dioxane (20 mL) and H2O (10 mL) was added dropwise conc. HCl (1.8 mL) at room temperature, and the mixture was stirred for 2 h. The reaction mixture was filtered and the filtrate was adjusted to pH˜8 by the addition of solid NaHCO3, and then extracted with ethyl acetate (50 mL). The organic layer was dried with Na2SO4, concentrated and the residue was purified by column chromatography (petroleum ether:ethyl acetate=20:1) to afford (S)-3-methoxy-5-(2-methylpyrrolidin-1-yl)benzenamine (269 mg, 72%) as yellow oil. LC-MS: 207 [M+H]+, tR=1.193 min.

Workup

  1. filtrationThe reaction mixture was filtered
  2. additionthe filtrate was adjusted to pH˜8 by the addition of solid NaHCO3
  3. extractionextracted with ethyl acetate (50 mL)
  4. dry with materialThe organic layer was dried with Na2SO4
  5. concentrationconcentrated
  6. customthe residue was purified by column chromatography (petroleum ether:ethyl acetate=20:1)

Sources & evidence

ORD record
ord-f8d915773dc9436199ac78d19d08a571
Source dataset
uspto-grants-2014_12
Patent number
US08921383B2

Linked notes

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