Sodium borohydride → 2(1H)-Quinazolinone, 3,4-dihydro-3-(1-(2-(4-chlorophenyl)-2-hydroxyethyl)-4-piperidinyl)-

HRID 67080Notes

Reaction equation

HRID 67080 reaction equation
[Cl:1][C:2]1[CH:27]=[CH:26][C:5]([C:6]([CH2:8][N:9]2[CH2:14][CH2:13][CH:12]([N:15]3[CH2:24][C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[NH:17][C:16]3=[O:25])[CH2:11][CH2:10]2)=[O:7])=[CH:4][CH:3]=1.[BH4-].[Na+]>CO>[Cl:1][C:2]1[CH:27]=[CH:26][C:5]([CH:6]([OH:7])[CH2:8][N:9]2[CH2:10][CH2:11][CH:12]([N:15]3[CH2:24][C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[NH:17][C:16]3=[O:25])[CH2:13][CH2:14]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 127979931-(4-Chlorobenzoylmethyl)-4-[3,4-dihydro-2(1H)-quinazolinon-3-yl]-piperidine

Product 1

HCID 30613872(1H)-Quinazolinone, 3,4-dihydro-3-(1-(2-(4-chlorophenyl)-2-hydroxyethyl)-4-piperidinyl)-Yield 58.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In this example, 2.70 g of 1-(4-chlorobenzoylmethyl)-4-[3,4-dihydro-2(1H)-quinazolinon-3-yl]-piperidine and 150 ml of methanol are mixed and stirred at room temperature. To the stirred mixture, 2.0 g of sodium borohydride is added over a period of 5 hours. Then, the resultant 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 2.07 g of a crude product. The crude product is recrystallized from a mixed solvent of chloroform and ethanol to obtain 1.59 g of the desired product.

Workup

  1. customThe white crystals deposited are separated by filtration
  2. washsuccessively washed with methanol and water
  3. customdried
  4. customto obtain 2.07 g of a crude product
  5. customThe crude product is recrystallized from a mixed solvent of chloroform and ethanol

Sources & evidence

ORD record
ord-992b58a31d184306a098a05d791f8bd3
Source dataset
uspto-grants-1982_08
Patent number
US04344948

Reaction notes

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