Nitrogen → 1-Methoxy-4-(3-n-propylamino)propyl-1,4-cyclohexadiene

HRID 542934Notes

Reaction equation

HRID 542934 reaction equation
[Li].[CH3:2][CH2:3][CH2:4][NH:5][CH2:6][CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=1.O.N#N>N.C(O)C.C1COCC1>[CH3:16][O:15][C:12]1[CH2:13][CH:14]=[C:9]([CH2:8][CH2:7][CH2:6][NH:5][CH2:4][CH2:3][CH3:2])[CH2:10][CH:11]=1

Participants

8

Reactant 4

HCID 947NitrogenHCID 962WaterHCID 3028194Lithium2×HCID 136504204-(3-n-Propylamino)propylanisole

Product 1

HCID 136504211-Methoxy-4-(3-n-propylamino)propyl-1,4-cyclohexadieneYield 93.5%

Reagents, catalysts & solvents 3

HCID 222AmmoniaSolvent2×HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution was prepared by dissolving 9.9 g of lithium in 2 l of anhydrous liquid ammonia. 98.7 g of 4-(3-n-propylamino)propylanisole were dissolved in a mixture of 27.8 ml of anhydrous ethanol and 300 ml of THF. This solution was added slowly in dropwise fashion with stirring to the lithium in liquid ammonia solution. After the addition has been completed, the reaction mixture was stirred for about 45 minutes. Water was then added slowly until the blue color of dissolved Li had been discharged. A stream of N2 was passed over the reaction mixture overnight to evaporate the ammonia. Additional water was then added to dissolve the salts which had formed. The alkaline aqueous solution was extracted three times with equal volumes of diethyl ether. The ethereal extracts were combined and dried. Evaporation of the ether yielded 93.2 g of 1-methoxy-4-(3-n-propylamino)propyl-1,4-cyclohexadiene; yield=93.5%.

Workup

  1. customA solution was prepared
  2. additionThis solution was added slowly in dropwise fashion
  3. additionAfter the addition
  4. customwas passed over the reaction mixture overnight
  5. customto evaporate the ammonia
  6. additionAdditional water was then added
  7. dissolutionto dissolve the salts which
  8. customhad formed
  9. extractionThe alkaline aqueous solution was extracted three times with equal volumes of diethyl ether
  10. customdried
  11. customEvaporation of the ether

Sources & evidence

ORD record
ord-c5fceed9044840f68e29e1157df4555f
Source dataset
uspto-grants-1987_04
Patent number
US04659832

Reaction notes

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