Triethylamine → 3-[4-(4-Hydroxy-phenyl)-piperazin-1-yl]-butyric acid methyl ester

HRID 12929

반응식

HRID 12929 반응식
[N:1]1([C:7]2[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.Br[CH:15]([CH3:21])[CH2:16][C:17]([O:19][CH3:20])=[O:18].C(N(CC)CC)C>CN(C=O)C>[CH3:20][O:19][C:17](=[O:18])[CH2:16][CH:15]([N:4]1[CH2:3][CH2:2][N:1]([C:7]2[CH:8]=[CH:9][C:10]([OH:13])=[CH:11][CH:12]=2)[CH2:6][CH2:5]1)[CH3:21]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 89470Butanoic acid, 3-bromo-, methyl esterHCID 92467p-(1-Piperazinyl)phenol

생성물 1

HCID 684326753-[4-(4-Hydroxy-phenyl)-piperazin-1-yl]-butyric acid methyl ester수율 59.3%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a mixture of 4-piperazin-1-yl-phenol (2 g, 11.2 mmol) and methyl 3-bromo-butyrate (2.03 g, 11.2 mmol) in DMF (5 mL) was added triethylamine (4.5 mL, 11.53 mmol) dropwise and the reaction mixture was stirred at ambient temperature overnight. The mixture was poured onto water and extracted with ethyl acetate (50 ml×3). The combined organic layers were washed with brine, dried over anhydrous Na2SO4 and evaporated under vacuum to dryness. The residue was purified by silica gel flash chromatography (1% methanol in CH2Cl2) to furnish the title compound (1.85 g, 59.3%); MS; m/z 279 (M+H).

후처리

  1. additionThe mixture was poured onto water
  2. extractionextracted with ethyl acetate (50 ml×3)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over anhydrous Na2SO4
  5. customevaporated under vacuum to dryness
  6. customThe residue was purified by silica gel flash chromatography (1% methanol in CH2Cl2)

출처 및 근거

ORD 기록
ord-8b0039b8c75446b48104676c801868df
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07728032B2

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