Acetic Acid → 1-(2-Bromophenyl)-4-cyclopropylmethylpiperazine

HRID 32269

반응식

HRID 32269 반응식
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1.C(O)(=O)C.[CH:18]1([CH:21]=O)[CH2:20][CH2:19]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])[O-].[K+].[K+]>O1CCCC1.C(OCC)(=O)C>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[CH2:13][CH2:12][N:11]([CH2:21][CH:18]2[CH2:20][CH2:19]2)[CH2:10][CH2:9]1

참가 물질

8

반응물 5

HCID 176Acetic AcidHCID 11430Potassium CarbonateHCID 123114CyclopropanecarboxaldehydeHCID 27571531-(2-Bromophenyl)piperazineHCID 5049666Sodium triacetoxyborohydride

생성물 1

HCID 231428391-(2-Bromophenyl)-4-cyclopropylmethylpiperazine수율 103.1%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 1-(2-bromophenyl)piperazine (3.0 g, 12.4 mmol) in tetrahydrofuran (30 mL) were added acetic acid (0.71 mL, 12.4 mmol), cyclopropanecarbaldehyde (1.39 mL, 18.66 mmol) and sodium triacetoxyborohydride (4.22 g, 19.9 mmol), followed by stirring for 88 hours at room temperature. Aqueous solution of potassium carbonate was added to the reaction mixture, extraction was performed with ethyl acetate, and the organic layer was concentrated. The resultant residue was purified by NH silica gel column chromatography (ethyl acetate/heptane) to give 3.773 g of the title compound as a colorless oil.

후처리

  1. concentrationthe organic layer was concentrated
  2. customThe resultant residue was purified by NH silica gel column chromatography (ethyl acetate/heptane)

출처 및 근거

ORD 기록
ord-c185f7e84db146ab9a55b333dfe511a7
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07425554B2

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