Acetic Acid → 1-(2-Cyclopropylethyl)-4-[2-(3,3,5,5-tetramethylcyclohexyl)phenyl]piperazine

HRID 32167

反応式

HRID 32167 の反応式
[CH:1]1([CH2:4][CH:5]=O)[CH2:3][CH2:2]1.[CH3:7][C:8]1([CH3:28])[CH2:13][C:12]([CH3:15])([CH3:14])[CH2:11][CH:10]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[N:22]2[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]2)[CH2:9]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C.C(=O)([O-])O.[Na+]>ClCCCl.C(OCC)(=O)C>[CH:1]1([CH2:4][CH2:5][N:25]2[CH2:26][CH2:27][N:22]([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=3[CH:10]3[CH2:11][C:12]([CH3:15])([CH3:14])[CH2:13][C:8]([CH3:28])([CH3:7])[CH2:9]3)[CH2:23][CH2:24]2)[CH2:3][CH2:2]1

参加物

8

反応物 5

HCID 176Acetic AcidHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 103078492-CyclopropylacetaldehydeHCID 119922841-[2-(3,3,5,5-Tetramethylcyclohexyl)phenyl]piperazine

生成物 1

HCID 231418781-(2-Cyclopropylethyl)-4-[2-(3,3,5,5-tetramethylcyclohexyl)phenyl]piperazine

試薬・触媒・溶媒 2

HCID 111,2-Dichloroethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of cyclopropylacetaldehyde in 1,2-dichloroethane (0.29 M, 5 mL) were added 1-[2-(3,3,5,5-tetramethylcyclohexyl)phenyl]piperazine (25 mg, 0.0832 mmol) produced in Example (8b), sodium triacetoxyborohydride (22.9 mg, 0.108 mmol) and acetic acid (0.009 mL, 0.158 mmol), followed by stirring for 20 minutes at room temperature. Saturated aqueous solution of sodium hydrogencarbonate was added to the reaction mixture and extraction was performed twice with ethyl acetate. The organic layer was concentrated and the resultant residue was purified by NH silica gel column chromatography (ethyl acetate/heptane) to give 20.9 mg of 1-(2-cyclopropylethyl)-4-[2-(3,3,5,5-tetramethylcyclohexyl)phenyl]piperazine 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-19b23eba74564111ab79266b31c81bff
出典データセット
uspto-grants-2008_09
特許番号
US07425554B2

関連ノート

読み込み中…