Triethylamine → N-(1,1-Diethyl-prop-2-ynyl)-4-[4-(2-methoxy-phenyl)-piperazin-1-yl]-2-phenyl-butyramide

HRID 2399700

반응식

HRID 2399700 반응식
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH:17]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:18](O)=[O:19])[CH2:11][CH2:10]1.C(N(CC)CC)C.O=C1N(N(N2CCOC2=O)P(Cl)(Cl)=O)CCO1.[CH3:51][CH2:52][C:53]([NH2:58])([C:56]#[CH:57])[CH2:54][CH3:55]>C(Cl)Cl>[CH2:54]([C:53]([NH:58][C:18](=[O:19])[CH:17]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH2:16][CH2:15][N:12]1[CH2:13][CH2:14][N:9]([C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[O:2][CH3:1])[CH2:10][CH2:11]1)([CH2:56][CH3:57])[C:52]#[CH:51])[CH3:55]

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 767103-Ethylpent-1-yn-3-amineHCID 98634284-[4-(2-Methoxyphenyl)piperazin-1-yl]-2-phenylbutanoic acidHCID 19975454N,N-bis(2-oxo-3oxazolidinyl)phosphoramidic chloride

생성물 1

HCID 15296374N-(1,1-Diethyl-prop-2-ynyl)-4-[4-(2-methoxy-phenyl)-piperazin-1-yl]-2-phenyl-butyramide수율 26.8%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A mixture of 4-[4-(2-methoxyphenyl)piperazin-1-yl]-2-phenylbutanoic acid (1.772 g, 5 mmole), triethylamine (1.518 g, 15 mmole), and N,N-bis(2-oxo-3-oxazolidinyl)phosphoramidic chloride (1.527 g, 6 mmole) was stirred in methylene chloride (80 mL) under exclusion of moisture at ambient temperature for 30 minutes, after which 1,1-diethylpropargylamine (0.668 g, 6 mmole) was added at once at 0° C. The reaction mixture was stirred at room temperature overnight, washed with water (2×100 mL), dried over magnesium sulfate, filtered, and evaporated to dryness in vacuo. Chromatography on silica gel with methanol/chloroform as eluant, followed by trituration from diethyl ether with addition of ethanolic hydrochloric acid gave 0.6 g of the title compound as the trihydrochloride hemihydrate, m.p. 110°-12° C.

후처리

  1. washwashed with water (2×100 mL)
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. customevaporated to dryness in vacuo
  5. additionChromatography on silica gel with methanol/chloroform as eluant, followed by trituration from diethyl ether with addition of ethanolic hydrochloric acid

출처 및 근거

ORD 기록
ord-cf7ea46d5e13469ab5cf8bc2154f4afc
출처 데이터셋
uspto-grants-1995_09
특허 번호
US05451584

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