Sodium Hydroxide → HCID 22732439, compound

HRID 2084165Notes

Reaction equation

HRID 2084165 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)=[C:5]([N+:15]([O-])=O)[CH:4]=1.[Sn](Cl)(Cl)(Cl)Cl.[OH-].[Na+]>C(O)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)=[C:5]([NH2:15])[CH:4]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24287Tin tetrachlorideHCID 2825430HCID 2825430, compound

Product 1

HCID 22732439HCID 22732439, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 1-(4-methoxy-2-nitrophenyl)piperidine (238 mg, 1.01 mmol) in anhydrous ethanol (20 ml) was slowly added anhydrous tin chloride (772 mg, 4.07 mmol) at room temperature. The mixture was refluxed for 1 h. The mixture was cooled to room temperature and then rotary evaporated to get an oily liquid. The liquid was basified with aqueous 2N NaOH (20 ml) to a final pH of 10. The resulting precipitate was filtered and washed with water. The aqueous solution was extracted with ethyl acetate (75 ml), washed with water (2×20 ml) and dried over anhydrous sodium sulfate. The ethyl acetate solution was rotary evaporated to give a dark brown liquid (153 mg, 74%). 1H NMR (CDCl3): 6.90 (d, J=8.7 Hz, 1H), 6.29 (d, J=2.7 Hz, 1H), 6.26 (dd, J=2.7, 8.1 Hz, 1H), 4.04 (bs, 2H), 3.69 (s, 3H), 2.75 (s, 4H), 1.70-1.63 (m, 4H), 1.54 (s, 2H).

Workup

  1. customat room temperature
  2. temperatureThe mixture was refluxed for 1 h
  3. customrotary evaporated
  4. customto get an oily liquid
  5. filtrationThe resulting precipitate was filtered
  6. washwashed with water
  7. extractionThe aqueous solution was extracted with ethyl acetate (75 ml)
  8. washwashed with water (2×20 ml)
  9. dry with materialdried over anhydrous sodium sulfate
  10. customThe ethyl acetate solution was rotary evaporated

Sources & evidence

ORD record
ord-6e2c18b53a004dd482249c177e509381
Source dataset
uspto-grants-2004_04
Patent number
US06716851B2

Reaction notes

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