Sodium Hydroxide → 1-Benzyl-4-(4-methoxyphenyl)-1,2,3,6-tetrahydropyridine

HRID 368834ノート

反応式

HRID 368834 の反応式
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=2)(O)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>C(OCC)(=O)C.ClCCl>[CH2:1]([N:8]1[CH2:9][CH:10]=[C:11]([C:15]2[CH:16]=[CH:17][C:18]([O:21][CH3:22])=[CH:19][CH:20]=2)[CH2:12][CH2:13]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

4

反応物 2

HCID 14798Sodium HydroxideHCID 159073291-Benzyl-4-(4-methoxyphenyl)piperidin-4-ol

生成物 1

HCID 106364031-Benzyl-4-(4-methoxyphenyl)-1,2,3,6-tetrahydropyridine

試薬・触媒・溶媒 1

HCID 21226138Dichloromethane ethylacetate溶媒

実験手順

A mixture of 1-benzyl-4-(4-methoxyphenyl)piperidin-4-ol (XIV, Step 1, 8.37 g, 28.1 mmol) and concentrated hydrochloric acid/H2O (1/1, 28 ml) is heated at 76° for 3 min. The resulting slurry is cooled and aqueous sodium hydroxide is added to make the mixture basic. The mixture is extracted several times with dichloromethane and the combined organic extracts are backwashed with saline, dried over magnesium sulfate, concentrated, and the resulting material chromatographed on silica gel eluting with methanol/dichloromethane (4/96). The appropriate fractions are pooled and concentrated to give 1-benzyl-1,2,3,6-tetrahydro-4-(4-methoxyphenyl)pyridine (XVI), MS (m/z) 279; IR (mineral oil) 1515, 738, 1030, 1258, 1250 and 1241 cm-1.

後処理

  1. temperatureis heated at 76° for 3 min
  2. temperatureThe resulting slurry is cooled
  3. extractionThe mixture is extracted several times with dichloromethane
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customthe resulting material chromatographed on silica gel eluting with methanol/dichloromethane (4/96)
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-8ccc810c48e0438fb13c292ce398d6a5
出典データセット
uspto-grants-2000_10
特許番号
US06133446

反応ノート

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