Potassium Carbonate → 1-(3-Butynyl)-4-(4-chlorophenyl)-4-hydroxypiperidine

HRID 324533ノート

反応式

HRID 324533 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([OH:14])[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH2:4]([N:11]1[CH2:10][CH2:9][C:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)([OH:14])[CH2:13][CH2:12]1)[CH2:3][C:2]#[CH:7]

参加物

4

反応物 2

HCID 11430Potassium CarbonateHCID 382824-(4-Chlorophenyl)-4-hydroxypiperidine

生成物 1

HCID 222257381-(3-Butynyl)-4-(4-chlorophenyl)-4-hydroxypiperidine収率 145.3%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

A mixutre of 3-butyn-1-methanesulfate (1.48 g, 0.01 mol), 4-(p-chlorophenyl)-4-hydroxypiperidine (2.54 g, 0.012 mol) and potassium carbonate (4.14 g, 0.03 mol) in 25 mL of acetonitrile was refluxed for 12 hrs. The mixture was filtered and washed with ethyl acetate (3×30 mL). The filtrate was evaporated in vacuo and was purified by flash chromatography to give 2.30 g (87%) of the product as a white solid. mp 98-100° C. 1H NMR (CHCl3) 1.550 (s, 1 H), 1.749 (m, 2 H), 1.997 (m, 1 H), 2.109 (m, 2 H), 2.423 (m, 4 H), 2.655 (m, 2 H), 2.798 (m, 2 H), 7.329 (d, J=7.2 Hz, 2 H), 7.429 (d, J=7.2 Hz, 2 H).

後処理

  1. filtrationThe mixture was filtered
  2. washwashed with ethyl acetate (3×30 mL)
  3. customThe filtrate was evaporated in vacuo
  4. customwas purified by flash chromatography

出典と根拠

ORDレコード
ord-a20d98fdbc614b749c5cf7f644d6bc42
出典データセット
uspto-grants-2001_04
特許番号
US06218404B1

反応ノート

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