Dimethylamine → N,N,1-Trimethyl-1,3,4,9-Tetrahydropyrano[3,4-b]Indole-1-Acetamide

HRID 1111601노트

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HRID 1111601 반응식
[CH3:1][C:2]1([CH2:15][C:16]([OH:18])=O)[C:7]2[NH:8][C:9]3[C:14]([C:6]=2[CH2:5][CH2:4][O:3]1)=[CH:13][CH:12]=[CH:11][CH:10]=3.[CH2:19]([N:21](CC)[CH2:22]C)C.ClC(OCC)=O.CNC>O1CCCC1>[CH3:19][N:21]([CH3:22])[C:16](=[O:18])[CH2:15][C:2]1([CH3:1])[C:7]2[NH:8][C:9]3[C:14]([C:6]=2[CH2:5][CH2:4][O:3]1)=[CH:13][CH:12]=[CH:11][CH:10]=3

참가 물질

6

반응물 4

HCID 674DimethylamineHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 104905711-Methyl-1,3,4,9-tetrahydropyrano[3,4-b]indole-1-acetic acid

생성물 1

HCID 12204534N,N,1-Trimethyl-1,3,4,9-Tetrahydropyrano[3,4-b]Indole-1-Acetamide

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
-5 °C

실험 절차

To a stirred solution of 1-methyl-1,3,4,9-tetrahydropyrano[3,4-b]indole-1-acetic acid (15 g, 0.061 mole), prepared as described In Example 1, in dry tetrahydrofuran (300 ml), cooled to -5° C., is added triethylamine (18.5 g, 0.183 mole), followed by ethyl chloroformate (16.6 g, 0.153 mole). The mixture is stirred at -5° C. for 2 hr. This mixture, which now contains the mixed anhydride of the above starting material, is added dropwise to a cooled 40% aqueous solution of the amine, dimethylamine (225 ml). The resulting mixture is stirred at room temperature for one-half hour. Most of the tetrahydrofuran is evaporated, and the residue partitioned between chloroform and water. The organic phase is washed with water, dried over sodium sulfate, and evaporated under reduced pressure. The residue is subjected to chromatography on silica gel. Elution with 20% ethyl acetate in benzene, followed by crystallization of the eluate from ethyl acetate affords the title compound, m.p. 149°-151° C., νmaxCHCl3 3375, 1634 cm-1.

후처리

  1. stirringThe resulting mixture is stirred at room temperature for one-half hour
  2. customMost of the tetrahydrofuran is evaporated
  3. customthe residue partitioned between chloroform and water
  4. washThe organic phase is washed with water
  5. dry with materialdried over sodium sulfate
  6. customevaporated under reduced pressure
  7. washElution with 20% ethyl acetate in benzene
  8. customfollowed by crystallization of the eluate from ethyl acetate

출처 및 근거

ORD 기록
ord-63f21865266048bb924a4ef4fe817330
출처 데이터셋
uspto-grants-1978_10
특허 번호
US04118394

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