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Benzylethanolamine → N-cyclohepty-5-[benzyl(2-hydroxyethyl)amino]pentanamide

HRID 610774
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HRID 610774 반응식
[CH:1]1([NH:8][C:9](=[O:15])[CH2:10][CH2:11][CH2:12][CH2:13]Br)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:16]([NH:23][CH2:24][CH2:25][OH:26])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH:1]1([NH:8][C:9](=[O:15])[CH2:10][CH2:11][CH2:12][CH2:13][N:23]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:24][CH2:25][OH:26])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1
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참가 물질

5

반응물 3

HCID 4348BenzylethanolamineHCID 11430Potassium CarbonateHCID 22125969n-Cycloheptyl-5-bromopentanamide

생성물 1

HCID 22125972N-cyclohepty-5-[benzyl(2-hydroxyethyl)amino]pentanamide수율 58.5%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

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온도
60 °C

실험 절차

N-cycloheptyl-5-bromopentanamide (4.15 g, 15 mmole) in solution in dimethylformamide (20 ml) is added dropwise to a hot solution (60° C.) of N-benzylethanolamine (2.27 g, 2.13 ml, 15 mmole) in dimethylformamide (25 ml) in the presence of potassium carbonate (4.15 g, 3 mmole). The reaction mixture is agitated for 2 hours at 60° C. then the solvent is evaporated under reduced pressure. The residue is taken up in dichloromethane (50 ml) and washed with water (3×30 ml). The organic phase is collected, dried over magnesium sulfate; the solvent is evaporated under reduced pressure. The product obtained is purified by flash chromatography over silica gel in a mixture of dichloromethane/methanol (90/10) to give 3.04 g (50%) of the expected compound in the form of an oil.

후처리

  1. customthe solvent is evaporated under reduced pressure
  2. washwashed with water (3×30 ml)
  3. customThe organic phase is collected
  4. dry with materialdried over magnesium sulfate
  5. customthe solvent is evaporated under reduced pressure
  6. customThe product obtained
  7. customis purified by flash chromatography over silica gel in a mixture of dichloromethane/methanol (90/10)

출처 및 근거

ORD 기록
ord-fadcc4f3ec5f43bab5e96e01299add98
출처 데이터셋
uspto-grants-1999_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05998666

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