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

HRID 32269

反応式

HRID 32269 の反応式
[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

参加物

8

反応物 5

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

生成物 1

HCID 231428391-(2-Bromophenyl)-4-cyclopropylmethylpiperazine収率 103.1%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-c185f7e84db146ab9a55b333dfe511a7
出典データセット
uspto-grants-2008_09
特許番号
US07425554B2

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