Triethylamine → 4-bromo-N-cyclohexyl-N-cyclopentylbenzamide

HRID 1588918노트

반응식

HRID 1588918 반응식
[CH:1]1([NH:6][CH:7]2[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[Br:20][C:21]1[CH:29]=[CH:28][C:24]([C:25](Cl)=[O:26])=[CH:23][CH:22]=1>O1CCCC1.O.C(OCC)(=O)C>[Br:20][C:21]1[CH:29]=[CH:28][C:24]([C:25]([N:6]([CH:7]2[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]2)[CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5]2)=[O:26])=[CH:23][CH:22]=1

참가 물질

7

반응물 3

HCID 8471TriethylamineHCID 685154-Bromobenzoyl chlorideHCID 219797n-Cyclopentylcyclohexanamine

생성물 1

HCID 197548884-bromo-N-cyclohexyl-N-cyclopentylbenzamide

시약·촉매·용매 3

HCID 962Water용매HCID 8028Tetrahydrofuran용매2회HCID 8857Ethyl Acetate용매

실험 절차

To a cold (+5° C.) stirred solution of N-cyclopentyl-N-cyclohexyl amine (4.0 g, 24 mmol) and triethylamine (2.5 g, 24 mmol) in tetrahydrofuran (50 ml) was added dropwise a solution of 4-bromobenzoyl chloride (5.0 g, 23 mmol) in tetrahydrofuran (20 ml). The reaction was stirred at room temperature overnight and worked up by diluting with water and ethyl acetate. The layers were separated and the organic layer was washed twice with 0.5N KHSO4, twice with 5% NaHCO3, and once with saturated aqueous NaCl solution. After drying over MgSO4, the drying agent was filtered, the filtrate concentrated in vacuo, and the residue recrystallized from cyclohexane to give the title compound: m. p. 110-112° C.

후처리

  1. customThe layers were separated
  2. washthe organic layer was washed twice with 0.5N KHSO4, twice with 5% NaHCO3
  3. dry with materialAfter drying over MgSO4
  4. filtrationthe drying agent was filtered
  5. concentrationthe filtrate concentrated in vacuo
  6. customthe residue recrystallized from cyclohexane

출처 및 근거

ORD 기록
ord-1bd458b98dbc4b7f9dab528fe9928102
출처 데이터셋
uspto-grants-1993_06
특허 번호
US05223539

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