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

HRID 1361512ノート

反応式

HRID 1361512 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

実験手順

To a solution of 2-bromo-4-chloro-1-methoxybenzene (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. at nitrogen atmosphere. After being stirred at this temperature for 1 h, 1-benzyl-piperidin-4-one (42 g, 0.22 mol) was added dropwise. After addition, the mixture was stirred at −78° C. for 1 h, and then warmed to room temperature. The reaction was quenched with NH4Cl (Sat. aq., 300 mL), and the separated aqueous layer was extracted with ethyl acetate (150 mL×3). The combined organic layer was 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 4b as white powder product. 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 −78° C. for 1 h
  3. customThe reaction was quenched with NH4Cl (Sat. aq., 300 mL)
  4. extractionthe separated aqueous layer was extracted with ethyl acetate (150 mL×3)
  5. washThe combined organic layer was washed with water and brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated to dryness
  8. customThe residue was purified by silica gel column

出典と根拠

ORDレコード
ord-973a607542da40de8e81f0f28046a167
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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