Aluminium lithium hydride → 4-(4-Bromophenyl)-4-(4-chlorophenyl)-1-methylpiperidine

HRID 924708ノート

反応式

HRID 924708 の反応式
C(O[C:4]([N:6]1[CH2:11][CH2:10][C:9]([C:19]2[CH:24]=[CH:23][C:22]([Br:25])=[CH:21][CH:20]=2)([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)[CH2:8][CH2:7]1)=O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[Br:25][C:22]1[CH:23]=[CH:24][C:19]([C:9]2([C:12]3[CH:13]=[CH:14][C:15]([Cl:18])=[CH:16][CH:17]=3)[CH2:10][CH2:11][N:6]([CH3:4])[CH2:7][CH2:8]2)=[CH:20][CH:21]=1

参加物

4

反応物 2

HCID 21226445Aluminium lithium hydrideHCID 59331961HCID 59331961、化合物

生成物 1

HCID 576913994-(4-Bromophenyl)-4-(4-chlorophenyl)-1-methylpiperidine収率 100.1%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Under a nitrogen atmosphere 4-(4-Bromo-phenyl)-4-(4-chloro-phenyl)-piperidine-1-carboxylic acid ethyl ester (0.28 g, 0.66 mmol) and lithium aluminum hydride (0.051 g) were suspended in tetrahydrofuran (5 ml) and stirred for 2 hours. The reaction mixture was quenched with addition of water, solvent removed under reduced pressure, the residue was partitioned between ethyl acetate and 2N NaOH. The organic layer was washed with brine, dried (MgSO4), filtered and concentrated to afford the desired product (0.241 g, 99% yield). LC/MS: (PS-B3) Rt 3.78 [M+H]+ 363.95, 365.73.

後処理

  1. customThe reaction mixture was quenched with addition of water, solvent
  2. customremoved under reduced pressure
  3. customthe residue was partitioned between ethyl acetate and 2N NaOH
  4. washThe organic layer was washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-11e89b241f914f9db9a223b73cbd140c
出典データセット
uspto-grants-2016_03
特許番号
US09283226B2

反応ノート

読み込み中…