Acetic Acid → 1-Butyl-4-(2-cyclooct-1-enylphenyl)piperazine

HRID 32159

反応式

HRID 32159 の反応式
[C:1]1([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[N:15]2[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]2)[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1.[CH:21](=O)[CH2:22][CH2:23][CH3:24].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C.C(=O)([O-])O.[Na+]>O1CCCC1.C(OCC)(=O)C>[CH2:21]([N:18]1[CH2:17][CH2:16][N:15]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[C:1]2[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=2)[CH2:20][CH2:19]1)[CH2:22][CH2:23][CH3:24]

参加物

8

反応物 5

HCID 176Acetic AcidHCID 261ButanalHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 692189821-(2-Cyclooct-1-enylphenyl)piperazine

生成物 1

HCID 692182621-Butyl-4-(2-cyclooct-1-enylphenyl)piperazine収率 74.5%

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-cyclooct-1-enylphenyl)piperazine (11 mg, 0.0407 mmol) produced in Example (46a) in tetrahydrofuran (1 mL) were added butyraldehyde (0.0047 mL, 0.0529 mmol), sodium triacetoxyborohydride (11.2 mg, 0.0529 mmol) and acetic acid (0.0044 mL, 0.0773 mmol), followed by stirring for 14 hours and 20 minutes at room temperature. Saturated aqueous solution of sodium hydrogencarbonate was added to the reaction mixture and extraction was performed three times with ethyl acetate. The organic layer was concentrated to produce a residue, which was purified by NH silica gel column chromatography (ethyl acetate/heptane) to give 9.9 mg of 1-butyl-4-(2-cyclooct-1-enylphenyl)piperazine as a colorless oil.

後処理

  1. concentrationThe organic layer was concentrated
  2. customto produce a residue, which
  3. customwas purified by NH silica gel column chromatography (ethyl acetate/heptane)

出典と根拠

ORDレコード
ord-13ec66df448c445f996b2d22352c8e59
出典データセット
uspto-grants-2008_09
特許番号
US07425554B2

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