N-(2-methylpropyl)-N-[(2,4-dichloro-1,3-thiazol-5-yl)methyl]piperidin-4-amine → [(4-Chloro-thiazol-5-yl)methyl]-isobutyl-piperidin-4-yl-amine

HRID 2111928ノート

反応式

HRID 2111928 の反応式
[Li]CCCC.Cl[C:7]1[S:8][C:9]([CH2:13][N:14]([CH2:21][CH:22]([CH3:24])[CH3:23])[CH:15]2[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]2)=[C:10]([Cl:12])[N:11]=1>O1CCCC1.C([O-])(O)=O.[Na+]>[CH3:23][CH:22]([CH3:24])[CH2:21][N:14]([CH2:13][C:9]1[S:8][CH:7]=[N:11][C:10]=1[Cl:12])[CH:15]1[CH2:16][CH2:17][NH:18][CH2:19][CH2:20]1

参加物

5

反応物 2

HCID 57640332N-(2-methylpropyl)-N-[(2,4-dichloro-1,3-thiazol-5-yl)methyl]piperidin-4-amineHCID 178418339Butyllithium

生成物 1

HCID 57640347[(4-Chloro-thiazol-5-yl)methyl]-isobutyl-piperidin-4-yl-amine収率 79.9%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 516892Sodium Bicarbonate溶媒2 回

反応条件

温度
-78 °C

実験手順

n-BuLi (1.6M in hexanes, 0.50 mL, 0.8 mmol) is added to a cold (−78° C.) solution of (2,4-dichloro-thiazol-5-ylmethyl)-isobutyl-piperdin-4-yl-amine (0.0995 g, 0.3 mmol) in anhydrous tetrahydrofuran. After stirring for 1 h at −78° C., aqueous saturated NaHCO3 is added, then poured in 100 mL aqueous saturated NaHCO3, extracted with ethyl acetate (3×100 mL). The layers are separated and the organic layer dried over Na2SO4, filtered, and concentrated. The crude material is purified on silica gel eluting with 1% NH4OH/10% ethanol/chloroform to yield (0.069 g, 78%) N-(2-methylpropyl)-N-[(4-chloro-1,3-thiazol-5-yl)methyl]piperidin-4-amine: mass spectrum (ion spray): m/z=288.1 (M+1); 1H NMR (CDCl3): δ=8.64 (1H, s), 3.81 (2H, s), 3.16 (2 H, brd), 2.60-2.49 (3H, m), 2.32 (2H, d), 1.82-1.62 (4H, m), 1.53-1.39 (2H, m), 0.91 (6H, d).

後処理

  1. extractionextracted with ethyl acetate (3×100 mL)
  2. customThe layers are separated
  3. dry with materialthe organic layer dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude material is purified on silica gel eluting with 1% NH4OH/10% ethanol/chloroform

出典と根拠

ORDレコード
ord-90e4bc138f37415badfe88e9f567d15f
出典データセット
uspto-grants-2009_04
特許番号
US07521462B2

反応ノート

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