Dimethylamine → N,N-dimethyl-[6-(anthraquinone-2-carbonyl)-4,5,6,7-tetrahydrofuro[2,3-c]pyridin-2-ylmethyl]amine

HRID 611138Notes

Reaction equation

HRID 611138 reaction equation
[CH:1]1[C:14]2[C:13](=[O:15])[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:6](=[O:16])[C:5]=2[CH:4]=[CH:3][C:2]=1[C:17]([N:19]1[CH2:24][CH2:23][C:22]2[CH:25]=[CH:26][O:27][C:21]=2[CH2:20]1)=[O:18].[CH3:28][NH:29][CH3:30].[CH2:31]=O>C(O)(=O)C>[CH3:28][N:29]([CH2:31][C:26]1[O:27][C:21]2[CH2:20][N:19]([C:17]([C:2]3[CH:3]=[CH:4][C:5]4[C:6](=[O:16])[C:7]5[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=5)[C:13](=[O:15])[C:14]=4[CH:1]=3)=[O:18])[CH2:24][CH2:23][C:22]=2[CH:25]=1)[CH3:30]

Participants

5

Reactant 3

HCID 674DimethylamineHCID 712FormaldehydeHCID 195999636-(Anthraquinone-2-carbonyl)-4,5,6,7-tetrahydrofuro[2,3-c]pyridine

Product 1

HCID 19599897N,N-dimethyl-[6-(anthraquinone-2-carbonyl)-4,5,6,7-tetrahydrofuro[2,3-c]pyridin-2-ylmethyl]amine

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 0.280 g (0.784 mmol) of 6-(anthraquinone-2-carbonyl)-4,5,6,7-tetrahydrofuro[2,3-c]pyridine in 20 ml of acetic acid, 0.106 ml (1.18 mmol) of 50% aqueous dimethylamine and 0.096 ml (1.18 mmol) of 37% aqueous formaldehyde were added, followed by stirring at 100° C. for 30 minutes. After the solvent was distilled off under reduced pressure, the residual solution was alkalified with 5% aqueous sodium hydrogen carbonate, and extracted with dichloromethane 2 times. The combined organic layer was washed with water and dried over anhydrous sodium sulfate; the solvent was distilled off under reduced pressure. The resulting crude product was purified by silica gel column chromatography (chloroform to chloroform/methanol=50/1) to yield the desired product.

Workup

  1. distillationAfter the solvent was distilled off under reduced pressure
  2. extractionextracted with dichloromethane 2 times
  3. washThe combined organic layer was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe resulting crude product was purified by silica gel column chromatography (chloroform to chloroform/methanol=50/1)

Sources & evidence

ORD record
ord-a6a86a1db4044efe98c723a003be3695
Source dataset
uspto-grants-1999_12
Patent number
US05998433

Reaction notes

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