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

HRID 1417815ノート

反応式

HRID 1417815 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-df5f274a4b4c4f17ab6a70d7e883880d
出典データセット
uspto-grants-1999_03
特許番号
US05877317

反応ノート

読み込み中…