Triethylamine → 2,2-dimethyl-N-(6,7,8,9-tetrahydro-dibenzofuran-2-yl)-propionamide

HRID 1819848노트

반응식

HRID 1819848 반응식
C(N(CC)CC)C.[CH:8]1[C:16]2[C:15]3[CH2:17][CH2:18][CH2:19][CH2:20][C:14]=3[O:13][C:12]=2[CH:11]=[CH:10][C:9]=1[NH2:21].[CH3:22][C:23]([CH3:28])([CH3:27])[C:24](Cl)=[O:25]>>[CH3:22][C:23]([CH3:28])([CH3:27])[C:24]([NH:21][C:9]1[CH:10]=[CH:11][C:12]2[O:13][C:14]3[CH2:20][CH2:19][CH2:18][CH2:17][C:15]=3[C:16]=2[CH:8]=1)=[O:25]

참가 물질

4

반응물 3

HCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 27947826,7,8,9-Tetrahydro-dibenzofuran-2-ylamine

생성물 1

HCID 248991902,2-dimethyl-N-(6,7,8,9-tetrahydro-dibenzofuran-2-yl)-propionamide수율 64.1%

반응 조건

온도
0 °C

실험 절차

Triethylamine (2.0 mL, 14 mmol) was added to a cooled (0° C.) solution of 6,7,8,9-tetrahydro-dibenzofuran-2-ylamine (0.86 g, 4.6 mmol). The reaction mixture was stirred for 10 minutes at 0° C. and then trimethylacetyl chloride (0.60 mL, 4.8 mmol) was added. The ice bath was removed and the reaction mixture was stirred for 30 min and then concentrated. The crude material was dissolved in chloroform and washed with 10% aqueous ammonium hydroxide, water, and brine, dried (Na2SO4) and concentrated. The crude material was recrystallized from acetonitrile to provide 2,2-dimethyl-N-(6,7,8,9-tetrahydro-dibenzofuran-2-yl)-propionamide (0.80 g). Mp 210-211° C.; Anal. Calcd. for C17H21NO2: C, 75.25; H, 7.80; N, 5.16; Found: C, 75.33; H, 7.64; N, 5.07.

후처리

  1. customThe ice bath was removed
  2. stirringthe reaction mixture was stirred for 30 min
  3. concentrationconcentrated
  4. dissolutionThe crude material was dissolved in chloroform
  5. washwashed with 10% aqueous ammonium hydroxide, water, and brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated
  8. customThe crude material was recrystallized from acetonitrile

출처 및 근거

ORD 기록
ord-179eee6e05734d1e85060be72eed9840
출처 데이터셋
uspto-grants-2009_10
특허 번호
US07601856B2

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