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 2111928노트

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HRID 2111928 반응식
[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

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 516892Sodium Bicarbonate용매2회

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온도
-78 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-90e4bc138f37415badfe88e9f567d15f
출처 데이터셋
uspto-grants-2009_04
특허 번호
US07521462B2

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