Sodium borohydride → 2(1H)-Quinazolinone, 3,4-dihydro-3-(1-(2-hydroxy-2-phenylethyl)-4-piperidinyl)-

HRID 67078Notes

Reaction equation

HRID 67078 reaction equation
[C:1]([CH2:9][N:10]1[CH2:15][CH2:14][CH:13]([N:16]2[CH2:25][C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[NH:18][C:17]2=[O:26])[CH2:12][CH2:11]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+]>CO>[C:2]1([CH:1]([OH:8])[CH2:9][N:10]2[CH2:11][CH2:12][CH:13]([N:16]3[CH2:25][C:24]4[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=4)[NH:18][C:17]3=[O:26])[CH2:14][CH2:15]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 12797991HCID 12797991, compound

Product 1

HCID 30613862(1H)-Quinazolinone, 3,4-dihydro-3-(1-(2-hydroxy-2-phenylethyl)-4-piperidinyl)-Yield 63.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In this example, 2.30 g of 1-benzoylmethyl-4-[3,4-dihydro-2(1H)-quinazolinon-3-yl]-piperidine and 100 ml of methanol are mixed and stirred at room temperature. To the stirred mixture, 1.5 g of sodium borohydride is added over a period of 5 hours. Then, the mixture is stirred overnight at room temperature. The white crystals deposited are separated by filtration, successively washed with methanol and water and dried to obtain 2.06 g of a crude product. The crude product is recrystallized from a mixed solvent of chloroform and ethanol to obtain 1.47 g of the desired product.

Workup

  1. stirringThen, the mixture is stirred overnight at room temperature
  2. customThe white crystals deposited are separated by filtration
  3. washsuccessively washed with methanol and water
  4. customdried
  5. customto obtain 2.06 g of a crude product
  6. customThe crude product is recrystallized from a mixed solvent of chloroform and ethanol

Sources & evidence

ORD record
ord-3b60b47fb05a42fd8732d7861d2d1c48
Source dataset
uspto-grants-1982_08
Patent number
US04344948

Reaction notes

Loading…