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

HRID 231313Notes

Reaction equation

HRID 231313 reaction equation
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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-78 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-9d94aa52a6f94522be50fbb6f5df93e1
Source dataset
uspto-grants-1989_07
Patent number
US04845221

Reaction notes

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