Thionyl Chloride → 1-Benzyl-3-[2-benzyloxy-4-(1,1-dimethylheptyl)phenyl]-4-(3-phenylpropyl)-1,2,5,6-tetrahydropyridine

HRID 444344ノート

反応式

HRID 444344 の反応式
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([CH2:15][CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)(O)[CH:10]([C:24]2[CH:29]=[CH:28][C:27]([C:30]([CH3:38])([CH3:37])[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])=[CH:26][C:25]=2[O:39][CH2:40][C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)(Cl)=O>N1C=CC=CC=1>[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([CH2:15][CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[C:10]([C:24]2[CH:29]=[CH:28][C:27]([C:30]([CH3:37])([CH3:38])[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])=[CH:26][C:25]=2[O:39][CH2:40][C:41]2[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

4

反応物 2

HCID 24386Thionyl ChlorideHCID 204997841-Benzyl-3-[2-benzyloxy-4-(1,1-dimethylheptyl)phenyl]-4-(3-phenylpropyl)-4-piperidinol

生成物 1

HCID 204997871-Benzyl-3-[2-benzyloxy-4-(1,1-dimethylheptyl)phenyl]-4-(3-phenylpropyl)-1,2,5,6-tetrahydropyridine

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

反応条件

温度
25 °C

実験手順

To a -5° C. solution of 3.0 g. (4.85 mmols.) of 1-benzyl-3-[2-benzyloxy-4-(1,1-dimethylheptyl)phenyl]-4-(3-phenylpropyl)-4-piperidinol in 5 ml. of pyridine is slowly added 2.89 g. (24.3 mmols.) of thionyl chloride. The reaction mixture is then allowed to slowly warm to 25° C. and is stirred 12 hours longers. The reaction mixture is quenched by slow addition to 200 ml. of cold 20% potassium carbonate. The quenched mixture is extracted with 250 ml. of ether, the extract washed once with 200 ml. 20% potassium carbonate, dried over magnesium sulfate and evaporated. THe residue is purified via column chromatography on 300 g. silica gel eluted with 50% ether-cyclohexane to yield the title compound.

後処理

  1. customTo a -5° C.
  2. customThe reaction mixture is quenched by slow addition to 200 ml
  3. extractionThe quenched mixture is extracted with 250 ml
  4. washof ether, the extract washed once with 200 ml
  5. dry with material20% potassium carbonate, dried over magnesium sulfate
  6. customevaporated
  7. customTHe residue is purified via column chromatography on 300 g
  8. washsilica gel eluted with 50% ether-cyclohexane

出典と根拠

ORDレコード
ord-43eb3099f642425ab5e03c6faa5d8adc
出典データセット
uspto-grants-1981_04
特許番号
US04263438

反応ノート

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