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

HRID 611343

反応式

HRID 611343 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.[C:11]1(/[C:17](=[CH:21]\[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)/[C:18](O)=[O:19])[CH:16]=[CH:15][CH:14]=[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>[CH3:28][N:30]([CH2:33][C:3]1[O:2][C:6]2[CH2:7][N:8]([C:18](=[O:19])/[C:17](/[C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[CH:21]/[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH2:9][CH2:10][C:5]=2[CH:4]=1)[CH3:31]

参加物

8

反応物 6

HCID 674DimethylamineHCID 712FormaldehydeHCID 8471TriethylamineHCID 76257Diethyl cyanophosphonateHCID 700620alpha-Phenylcinnamic acid, (E)-HCID 195999074,5,6,7-Tetrahydrofuro[2,3-c]pyridine hydrochloride

生成物 1

HCID 19599936(E)-N,N-dimethyl-[6-(2,3-diphenylpropenoyl)-4,5,6,7-tetrahydrofuro[2,3-c]pyridin-2-ylmethyl]amine

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of 0.319 g (2.000 mmol) of 4,5,6,7-tetrahydrofuro[2,3-c]pyridine hydrochloride, 0.493 g (2.2 mmol) of (E)-2,3-diphenylpropenoic acid and 1.1 ml (8.0 mmol) of triethylamine in 30 ml of dichloromethane, 0.489 g (3.0 mmol) of diethyl cyanophosphonate was added dropwise under ice-cooling, followed by overnight stirring at room temperature. After the solvent was distilled off, water was added, followed by 2 extractions with ethyl acetate. 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; 0.270 ml (3.00 mmol) of 50% aqueous dimethylamine and 0.245 ml (3.00 mmol) of 37% aqueous formaldehyde were added, followed by stirring at 100° C. for 120 minutes. After the solvent was distilled off under reduced pressure, the residual solution was alkalified with 5% aqueous sodium hydrogen carbonate and extracted with ethyl acetate 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. distillationAfter the solvent was distilled off
  3. additionwater was added
  4. extractionfollowed by 2 extractions with ethyl acetate
  5. washThe combined organic layer was washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationthe solvent was distilled off under reduced pressure
  8. dissolutionThe resulting crude product was dissolved in 10 ml of acetic acid
  9. stirringby stirring at 100° C. for 120 minutes
  10. distillationAfter the solvent was distilled off under reduced pressure
  11. extractionextracted with ethyl acetate 2 times
  12. washThe combined organic layer was washed with water
  13. dry with materialdried over anhydrous sodium sulfate
  14. distillationthe solvent was distilled off under reduced pressure
  15. 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-c9e3d1dc12c646c1af9cf2a9a0d53094
出典データセット
uspto-grants-1999_12
特許番号
US05998433

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