Acetic Acid → (+/-)-cis-6-(3,4-Dimethoxyphenyl)-cyclohex-3-enylamine

HRID 731688Notes

Reaction equation

HRID 731688 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C@@H:9]2[CH2:14][CH:13]=[CH:12][CH2:11][C@@H:10]2[N+:15]([O-])=O)=[CH:5][C:4]=1[O:18][CH3:19].C(O)(=O)C>C(O)C.[Zn]>[CH3:19][O:18][C:4]1[CH:5]=[C:6]([C@@H:9]2[C@H:10]([NH2:15])[CH2:11][CH:12]=[CH:13][CH2:14]2)[CH:7]=[CH:8][C:3]=1[O:2][CH3:1]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 15389588(+/-)-cis-1 2-Dimethoxy-4-(2-nitrocyclohex-4-enyl)benzene

Product 1

HCID 86601281(+/-)-cis-6-(3,4-Dimethoxyphenyl)-cyclohex-3-enylamineYield 32.4%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 702EthanolSolvent

Procedure

40 g of (±)-cis-1,2-dimethoxy-4-(2-nitrocyclohex-4-enyl)benzene (compound I7) are dissolved in 400 ml of ethanol and 40 g of zinc powder are added. After heating to boiling temperature, 65 ml of glacial acetic acid are added dropwise. Afterwards, the reaction mixture is filtrated and concentrated. The residue is redissolved in diluted hydrochloric acid and extracted with toluene. The aqueous layer is alkalized using 6 N solution of sodium hydroxide and extracted several times with toluene. The combined organic phases of the alkalic extraction are dried using sodium sulfate and concentrated. The residue is chromatographed on silica gel. 11.5 g of the title compound are obtained.

Workup

  1. temperatureAfter heating
  2. additionare added dropwise
  3. filtrationAfterwards, the reaction mixture is filtrated
  4. concentrationconcentrated
  5. dissolutionThe residue is redissolved in diluted hydrochloric acid
  6. extractionextracted with toluene
  7. extractionextracted several times with toluene
  8. extractionThe combined organic phases of the alkalic extraction
  9. customare dried
  10. concentrationconcentrated
  11. customThe residue is chromatographed on silica gel

Sources & evidence

ORD record
ord-aff12d1029854a0e9df065a7060da31a
Source dataset
uspto-grants-2009_09
Patent number
US07585872B2

Reaction notes

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