Dimethylamine → N,N-Dimethyl-[6-(9-fluorenone-2-carbonyl)-4,5,6,7-tetrahydrofuro[2,3-c]pyridin-2-ylmethyl]amine

HRID 611337

反応式

HRID 611337 の反応式
Cl.[O:2]1[C:6]2[CH2:7][NH:8][CH2:9][CH2:10][C:5]=2[CH:4]=[CH:3]1.[CH:11]1[CH:16]=[C:15]2[C:17]3[CH:24]=[CH:23][C:22]([C:25]([OH:27])=O)=[CH:21][C:18]=3[C:19](=[O:20])[C:14]2=[CH:13][CH:12]=1.[CH2:28]([N:30]([CH2:33]C)[CH2:31]C)C.C(P(=O)(OCC)OCC)#N.CNC.C=O>ClCCl.O>[CH3:28][N:30]([CH2:33][C:3]1[O:2][C:6]2[CH2:7][N:8]([C:25]([C:22]3[CH:23]=[CH:24][C:17]4[C:15]5[C:14](=[CH:13][CH:12]=[CH:11][CH:16]=5)[C:19](=[O:20])[C:18]=4[CH:21]=3)=[O:27])[CH2:9][CH2:10][C:5]=2[CH:4]=1)[CH3:31]

参加物

9

反応物 6

HCID 674DimethylamineHCID 712FormaldehydeHCID 8471TriethylamineHCID 69913Fluorenone-2-carboxylic acidHCID 76257Diethyl cyanophosphonateHCID 195999074,5,6,7-Tetrahydrofuro[2,3-c]pyridine hydrochloride

生成物 1

HCID 19599904N,N-Dimethyl-[6-(9-fluorenone-2-carbonyl)-4,5,6,7-tetrahydrofuro[2,3-c]pyridin-2-ylmethyl]amine

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

To a solution of 0.160 g (1.000 mmol) of 4,5,6,7-tetrahydrofuro[2,3-c]pyridine hydrochloride, 0.246 g (1.1 mmol) of 9-fluorenone-2-carboxylic acid and 0.55 ml (4.0 mmol) of triethylamine in 30 ml of dichloromethane, 0.24 g (1.5 mmol) of diethyl cyanophosphonate was added dropwise under ice-cooling, followed by overnight stirring at room temperature. This mixture was poured into water, followed by 2 extractions with dichloromethane. 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 dissolved in 10 ml of acetic acid; 0.135 ml (1.50 mmol) of 50% aqueous dimethylamine and 0.122 ml (1.50 mmol) of 37% aqueous formaldehyde were added, followed by stirring at 100° C. for 60 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 (ethyl acetate/methanol=5/1) to yield the desired product.

後処理

  1. temperaturecooling
  2. extractionfollowed by 2 extractions with dichloromethane
  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. dissolutionThe resulting crude product was dissolved in 10 ml of acetic acid
  7. stirringby stirring at 100° C. for 60 minutes
  8. distillationAfter the solvent was distilled off under reduced pressure
  9. extractionextracted with dichloromethane 2 times
  10. washThe combined organic layer was washed with water
  11. dry with materialdried over anhydrous sodium sulfate
  12. distillationthe solvent was distilled off under reduced pressure
  13. customThe resulting crude product was purified by silica gel column chromatography (ethyl acetate/methanol=5/1)

出典と根拠

ORDレコード
ord-d3e79e3b02674805b10bae4dcbac1a6b
出典データセット
uspto-grants-1999_12
特許番号
US05998433

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