Dimethylamine → N,N-Dimethyl-[6-(1-benzoylpiperidine-4-carbonyl)-4,5,6,7-tetrahydrofuro[2,3-c]pyridin-2-ylmethyl]amine

HRID 611347

反応式

HRID 611347 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]([N:19]1[CH2:24][CH2:23][CH:22]([C:25]([OH:27])=O)[CH2:21][CH2:20]1)(=[O:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[CH2:28]([N:30]([CH2:33]C)[CH2:31]C)C.C(P(=O)(OCC)OCC)#N.CNC.C=O>CN(C)C=O.O>[CH3:28][N:30]([CH2:33][C:3]1[O:2][C:6]2[CH2:7][N:8]([C:25]([CH:22]3[CH2:23][CH2:24][N:19]([C:11](=[O:18])[C:12]4[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=4)[CH2:20][CH2:21]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 76257Diethyl cyanophosphonateHCID 789351-Benzoylpiperidine-4-carboxylic acidHCID 195999074,5,6,7-Tetrahydrofuro[2,3-c]pyridine hydrochloride

生成物 1

HCID 19600056N,N-Dimethyl-[6-(1-benzoylpiperidine-4-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 6228Dimethylformamide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, 0.513 g (2.2 mmol) of 1-benzoyl-4-piperidinecarboxylic acid and 1.1 ml (8.0 mmol) of triethylamine in 30 ml of N,N-dimethylformamide, 0.489 g (3.0 mmol) of diethyl cyanophosphonate was added dropwise under ice-cooling, followed by overnight stirring at room temperature. 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 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 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=4/1) to yield the desired product.

後処理

  1. temperaturecooling
  2. extractionfollowed by 2 extractions with ethyl acetate
  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 30 minutes
  8. distillationAfter the solvent was distilled off under reduced pressure
  9. extractionextracted with ethyl acetate 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=4/1)

出典と根拠

ORDレコード
ord-1023eb4a82854d64a140abbbc19e6dd6
出典データセット
uspto-grants-1999_12
特許番号
US05998433

関連ノート

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