1-Benzyl-4-piperidone → HCID 58772035、化合物

HRID 1361508ノート

反応式

HRID 1361508 の反応式
Br[C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[O:9][CH3:10].[Li]CCCC.[CH2:16]([N:23]1[CH2:28][CH2:27][C:26](=[O:29])[CH2:25][CH2:24]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C1COCC1>[CH2:16]([N:23]1[CH2:28][CH2:27][C:26]([C:2]2[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=2[O:9][CH3:10])([OH:29])[CH2:25][CH2:24]1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

参加物

5

反応物 3

HCID 192201-Benzyl-4-piperidoneHCID 5219352-Bromo-4-chloroanisoleHCID 178418339Butyllithium

生成物 1

HCID 58772035HCID 58772035、化合物

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

To a solution of 2-bromo-4-chloroanisole (1a, 51 g, 0.23 mol) in THF (500 mL) was added dropwise n-BuLi (2.5 M in hexane, 138 mL, 0.345 mol) at −78° C. under nitrogen atmosphere. After being stirred at −78° C. for 1 h, 1-benzyl-piperidin-4-one (42 g, 0.22 mol) was added dropwise. After addition, the mixture was stirred at this temperature for 1 h, and then warmed to room temperature. The reaction was quenched with saturated NH4Cl (300 mL) and the separated aqueous layer was extracted with ethyl acetate (150 mL×3). The combined extracts were washed with water and brine, dried over Na2SO4, concentrated to dryness. The residue was purified by silica gel column to obtain 1-benzyl-4-(5-chloro-2-methoxy-phenyl)-piperidin-4-ol 1b as a white solid. 1H NMR (CDCl3): δ 7.37-7.24 (m, 6H), 7.21 (q, J1=8.8 Hz, J2=2.8 Hz, 1H), 6.85 (d, J=8.8 Hz, 1H), 3.88 (s, 3H), 3.80 (s, 1H), 3.59 (s, 2, H), 2.77-2.74 (m, 2, H), 2.59-2.54 (t, 2H), 2.13-2.06 (m, 2H), 2.00-1.96 (m, 2H).

後処理

  1. additionAfter addition
  2. stirringthe mixture was stirred at this temperature for 1 h
  3. temperaturewarmed to room temperature
  4. customThe reaction was quenched with saturated NH4Cl (300 mL)
  5. extractionthe separated aqueous layer was extracted with ethyl acetate (150 mL×3)
  6. washThe combined extracts were washed with water and brine
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated to dryness
  9. customThe residue was purified by silica gel column

出典と根拠

ORDレコード
ord-5f381344ca6a4df9a8c762a4f23702b6
出典データセット
uspto-grants-2011_02
特許番号
US07880007B2

反応ノート

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