1-(2-(3-Nitrophenoxy)ethyl)pyrrolidine → 3-[2-(Pyrrolidin-1-yl)ethoxy]aniline

HRID 1635797Notes

Reaction equation

HRID 1635797 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:15]=[CH:16][CH:17]=1)[O:7][CH2:8][CH2:9][N:10]1[CH2:14][CH2:13][CH2:12][CH2:11]1)([O-])=O.[H][H]>[Pd].C(OCC)(=O)C>[NH2:1][C:4]1[CH:5]=[C:6]([CH:15]=[CH:16][CH:17]=1)[O:7][CH2:8][CH2:9][N:10]1[CH2:14][CH2:13][CH2:12][CH2:11]1

Participants

5

Reactant 2

HCID 219416871-(2-(3-Nitrophenoxy)ethyl)pyrrolidineHCID 178418361HCID 178418361, compound

Product 1

HCID 219416963-[2-(Pyrrolidin-1-yl)ethoxy]aniline

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1-(2-(3-nitrophenoxy)ethyl)pyrrolidine (3.49 g, 14.8 mmol), 10% palladium on carbon (400 mg) and ethyl acetate (20 ml) was reduced under 50 psi hydrogen for 10 h. The reaction mixture was filtered through Celite 545 and the product extracted into 1M HCl (3×20 ml). The acidic layer was washed with ether (2×20 ml) and then the pH adjusted to >10 with 2M NaOH. The aqueous layer was extracted with ether (3×20 ml), dried over MgSO4 and concentrated in vacuo. The product was eluted through a silica gel pad (75% ethyl acetate/hexane/1% Et3N) to yield the product as a pale yellow oil.

Workup

  1. filtrationThe reaction mixture was filtered through Celite 545
  2. extractionthe product extracted into 1M HCl (3×20 ml)
  3. washThe acidic layer was washed with ether (2×20 ml)
  4. extractionThe aqueous layer was extracted with ether (3×20 ml)
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. washThe product was eluted through a silica gel pad (75% ethyl acetate/hexane/1% Et3N)

Sources & evidence

ORD record
ord-34cba73713bd4e0abda9d1867bb8d787
Source dataset
uspto-grants-2003_01
Patent number
US06511980B2

Reaction notes

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