Sodium Bicarbonate → 2-[4-(1,2,3,4-Tetrahydro-8-hydroxy-2-naphthalenyl)-1-piperazinyl]pyrimidine

HRID 231313

반응식

HRID 231313 반응식
Cl.C[O:3][C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:13]=1[CH2:12][CH:11]([N:14]1[CH2:19][CH2:18][N:17]([C:20]3[N:25]=[CH:24][CH:23]=[CH:22][N:21]=3)[CH2:16][CH2:15]1)[CH2:10][CH2:9]2.[B].C([O-])(O)=O.[Na+]>C(Cl)Cl>[OH:3][C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:13]=1[CH2:12][CH:11]([N:14]1[CH2:19][CH2:18][N:17]([C:20]3[N:21]=[CH:22][CH:23]=[CH:24][N:25]=3)[CH2:16][CH2:15]1)[CH2:10][CH2:9]2

참가 물질

5

반응물 3

HCID 516892Sodium BicarbonateHCID 5462311BoronHCID 144799992-(4-(1,2,3,4-Tetrahydro-8-methoxy-2-naphthalenyl)-1-piperazinyl]-pyrimidine hydrochloride

생성물 1

HCID 144800022-[4-(1,2,3,4-Tetrahydro-8-hydroxy-2-naphthalenyl)-1-piperazinyl]pyrimidine수율 70.9%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

반응 조건

온도
-78 °C

실험 절차

2-(4-(1,2,3,4-Tetrahydro-8-methoxy-2-naphthalenyl)-1-piperazinyl]-pyrimidine hydrochloride (1.62 g, 5.0 mmole) was dissolved in 185 ml of methylene chloride and cooled to -78° C. in a dry ice/acetone bath. A mixture of 15 ml of 1 M boron triboromide and 15 ml of methylene chloride was added. The reaction mixture was allowed to come to room temperature and it was then stirred for three days. The reaction was then poured into a saturated NaHCO3 solution and the product extracted with 600 ml of chloroform. This solution was dried over MgSO4, filtered, and concentrated in vacuum. The residue was column chromatographed on 100 g of silica gel with 5% methanol/chloroform and the crude title compound thus obtained was crystallized from isopropanol with addition of 4 N isopropanolic HCl and recrystallized from acetone to give 1.1 g of the title compound as the hydrochloride, monohydrate, m.p.>300° C.

후처리

  1. additionwas added
  2. customto come to room temperature
  3. extractionthe product extracted with 600 ml of chloroform
  4. dry with materialThis solution was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuum
  7. customchromatographed on 100 g of silica gel with 5% methanol/chloroform
  8. customthe crude title compound thus obtained
  9. customwas crystallized from isopropanol with addition of 4 N isopropanolic HCl
  10. customrecrystallized from acetone

출처 및 근거

ORD 기록
ord-9d94aa52a6f94522be50fbb6f5df93e1
출처 데이터셋
uspto-grants-1989_07
특허 번호
US04845221

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