1-(3-(Trifluoromethyl)phenyl)piperazine → 2-ethyl-3-(2-(4-(3-(trifluoromethyl)phenyl)piperazine-1-yl)ethyl)quinazoline-4(3H)-one

HRID 1028347노트

반응식

HRID 1028347 반응식
Cl[CH2:2][CH2:3][N:4]1[C:13](=[O:14])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]=[C:5]1[CH2:15][CH3:16].[F:17][C:18]([F:32])([F:31])[C:19]1[CH:20]=[C:21]([N:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)[CH:22]=[CH:23][CH:24]=1.C(=O)([O-])[O-].[Na+].[Na+].[I-].[Na+]>C(O)(=O)C.C1(C)C=CC=CC=1.C(O)C>[CH2:15]([C:5]1[N:4]([CH2:3][CH2:2][N:28]2[CH2:27][CH2:26][N:25]([C:21]3[CH:22]=[CH:23][CH:24]=[C:19]([C:18]([F:31])([F:32])[F:17])[CH:20]=3)[CH2:30][CH2:29]2)[C:13](=[O:14])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]=1)[CH3:16]

참가 물질

8

반응물 4

HCID 42961-(3-(Trifluoromethyl)phenyl)piperazineHCID 5238Sodium IodideHCID 10340Sodium CarbonateHCID 597239043-(2-Chloroethyl)-2-ethyl-3,4-dihydro-4-quinazolinone

생성물 1

HCID 668251862-ethyl-3-(2-(4-(3-(trifluoromethyl)phenyl)piperazine-1-yl)ethyl)quinazoline-4(3H)-one수율 98.9%

시약·촉매·용매 3

HCID 176Acetic Acid용매HCID 702Ethanol용매HCID 1140Toluene용매

실험 절차

3-(2-chloroethyl)-2-ethylquinazoline-4 (3H)-one (1.5 g; 6.34 mmol), 1-(3-(trifluoromethyl)phenyl)piperazine (1.459 g; 6.34 mmol), sodium carbonate (0.672 g; 6.34 mmol), sodium iodide (0.95 g; 6.34 mmol), ethanol (100 mL) and toluene (200 mL) were added to a 100 mL reactor. The reaction medium was heated to reflux and kept under agitation for a period of 24 hours, during which 250 mL of solvent were slowly removed with assistance from a Dean Stark. The reaction was monitored through CG/MS until completion. After the end of the reaction, ethyl acetate (250 mL) was added, together with an aqueous solution of acetic acid (100 mL; 10%). The mixture was maintained under agitation for a period of 30 minutes. The organic phase was separated, washed with two portions of 50 mL of NaHCO3 at 5%, dried with MgSO4 and evaporated at reduced pressure, yielding a pale yellow colored oil (2.7 g of raw 2-ethyl-3-(2-(4-(3-(trifluoromethyl)phenyl)piperazine-1-yl)ethyl) quinazoline-4 (3H)-one). This oil was dissolved in isopropanol, adding 2.0 mL of concentrated HCl to the resulting solution. The solution was kept under agitation at room temperature, until completing precipitation of the solids. The solids were vacuum filtered, washed with two portions of 5 mL of isopropanol and dried, yielding 2-ethyl-3-(2-(4-(3-(trifluoromethyl)phenyl)piperazine-1-yl)ethyl)quinazoline-4 (3H)-one hydrochloride as a pale white solid (2.36 g, 5.48 mmol, yield: 87%).

후처리

  1. temperatureThe reaction medium was heated
  2. temperatureto reflux
  3. customwere slowly removed with assistance from a Dean Stark
  4. customAfter the end of the reaction, ethyl acetate (250 mL)
  5. temperatureThe mixture was maintained under agitation for a period of 30 minutes
  6. customThe organic phase was separated
  7. washwashed with two portions of 50 mL of NaHCO3 at 5%
  8. dry with materialdried with MgSO4
  9. customevaporated at reduced pressure

출처 및 근거

ORD 기록
ord-2d4c7e70a6ad48248822991dbafd9b38
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08735578B2

반응 노트

불러오는 중…