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

HRID 1063782Notes

Reaction equation

HRID 1063782 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-1c0e295540bb4dabb7c237d8e9ae8698
Source dataset
uspto-grants-2005_11
Patent number
US06967199B2

Reaction notes

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