Diphenylphosphinic chloride → 4-[2-(4-Geranyloxybenzoylamino)ethyl]pyridine

HRID 850400노트

반응식

HRID 850400 반응식
[CH2:1]([O:11][C:12]1[CH:20]=[CH:19][C:15]([C:16]([OH:18])=O)=[CH:14][CH:13]=1)/[CH:2]=[C:3](/[CH2:5][CH2:6][CH:7]=[C:8]([CH3:10])[CH3:9])\[CH3:4].C1(P(Cl)(C2C=CC=CC=2)=O)C=CC=CC=1.[NH2:36][CH2:37][CH2:38][C:39]1[CH:44]=[CH:43][N:42]=[CH:41][CH:40]=1>C(Cl)(Cl)Cl.C(N(CC)CC)C>[CH2:1]([O:11][C:12]1[CH:13]=[CH:14][C:15]([C:16]([NH:36][CH2:37][CH2:38][C:39]2[CH:44]=[CH:43][N:42]=[CH:41][CH:40]=2)=[O:18])=[CH:19][CH:20]=1)/[CH:2]=[C:3](/[CH2:5][CH2:6][CH:7]=[C:8]([CH3:9])[CH3:10])\[CH3:4]

참가 물질

6

반응물 3

HCID 73910Diphenylphosphinic chlorideHCID 832754-PyridineethanamineHCID 123615004-Geranyloxybenzoic acid

생성물 1

HCID 99296694-[2-(4-Geranyloxybenzoylamino)ethyl]pyridine수율 85.3%

시약·촉매·용매 2

HCID 6212Chloroform용매HCID 8471Triethylamine용매

실험 절차

4-geranyloxybenzoic acid(1.92 g) was dissolved in chloroform(50 ml) and triethylamine(1.96 ml), and then diphenylphosphinic chloride(1.33 ml) was added thereto while being cooled with ice. After being stirred for 30 minutes, the mixture, with 4-(2-aminoethyl)pyridine(0.94 g) added thereto, was stirred for 2 hours at room temperature. The reaction mixture was washed with saturated sodium hydrogencarbonate aqueous solution and saturated brine successively, dried over sodium sulfate anhydride, and then concentrated under a vacuum. The residue was purified by silica gel column chromatography (chloroform:methanol=30:1), thereby yielding 2.26 g of the aimed compound.

후처리

  1. temperaturewhile being cooled with ice
  2. stirringwas stirred for 2 hours at room temperature
  3. washThe reaction mixture was washed with saturated sodium hydrogencarbonate aqueous solution and saturated brine successively
  4. dry with materialdried over sodium sulfate anhydride
  5. concentrationconcentrated under a vacuum
  6. customThe residue was purified by silica gel column chromatography (chloroform:methanol=30:1)

출처 및 근거

ORD 기록
ord-548c05eaa5b944c19c87e05f69f48e27
출처 데이터셋
uspto-grants-2000_01
특허 번호
US06017937

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