Hydrochloric Acid → 2-[4-(1,2,3,4-Tetrahydro-8-methoxy-2-naphthalenyl)-1-piperazinyl]pyrimidine

HRID 231311노트

반응식

HRID 231311 반응식
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[CH2:11][C:10](=O)[CH2:9][CH2:8]2.Cl.Cl.[N:16]1[CH:21]=[CH:20][CH:19]=[N:18][C:17]=1[N:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(N(C(C)C)CC)(C)C.Cl.C([BH3-])#N.C([N+](CCCC)(CCCC)CCCC)CCC>C1(C)C=CC=CC=1.O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[CH2:11][CH:10]([N:25]1[CH2:26][CH2:27][N:22]([C:17]3[N:16]=[CH:21][CH:20]=[CH:19][N:18]=3)[CH2:23][CH2:24]1)[CH2:9][CH2:8]2

참가 물질

9

반응물 6

HCID 313Hydrochloric AcidHCID 6101p-Toluenesulfonic acidHCID 81531DiisopropylethylamineHCID 2724287Tetrabutylammonium (cyano-C)trihydroborateHCID 41360218-Methoxy-2-tetraloneHCID 116802722-Piperazinylpyrimidine dihydrochloride

생성물 1

HCID 144799982-[4-(1,2,3,4-Tetrahydro-8-methoxy-2-naphthalenyl)-1-piperazinyl]pyrimidine수율 30.8%

시약·촉매·용매 2

HCID 962Water용매HCID 1140Toluene용매

실험 절차

8-Methoxy-2-tetralone (3.5 g, 20 mmole), 1-(2-pyrimidinyl) piperazine dihydrochloride (4.6 g, 20 mmole), 0.38 g of p-toluenesulfonic acid and 3.48 ml of diisopropylethylamine were combined in 200 ml of toluene and the mixture refluxed under N2 for three days with water removal via a Dean-Stark trap. After the reaction had cooled, 10.5 ml of 4 N isopropanolic HCl was added, followed in portions by 5.93 g of tetra-n-butyl ammonium cyanoborohydride. The mixture was refluxed under N2 for one hour and the solvent removed in vacuum. The residue was redissolved in 300 ml of CHCl3, washed with saturated NaHCO3 solution, dried over MgSO4, filtered, and evaporated in vacuum. The crude product was column chromatographed on 75 g of silica gel employing chloroform as the eluent and the relevant fractions were combined and concentrated in vacuum. The crude title compound was crystallized from 50 ml of isopropanol with addition of 4 N isopropanolic HCl to obtain 2.0 g of the title compound as the monohydrochloride. A second crystallization from isopropanol gave 1.3 g of monohydrochloride, m.p. 273°-276° C. (d).

후처리

  1. temperatureAfter the reaction had cooled
  2. temperatureThe mixture was refluxed under N2 for one hour
  3. customthe solvent removed in vacuum
  4. dissolutionThe residue was redissolved in 300 ml of CHCl3
  5. washwashed with saturated NaHCO3 solution
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customevaporated in vacuum
  9. customchromatographed on 75 g of silica gel
  10. concentrationconcentrated in vacuum
  11. customThe crude title compound was crystallized from 50 ml of isopropanol with addition of 4 N isopropanolic HCl

출처 및 근거

ORD 기록
ord-6f63797e1c154b1e9e37ab59f6d766ab
출처 데이터셋
uspto-grants-1989_07
특허 번호
US04845221

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