Sodium borohydride → 1-[2-(3,4-Dimethoxyphenyl)-2-hydroxyethyl]-4-[3,4-dihydro-2(1H)-quinazolinon-3-yl]-piperidine

HRID 67072Notes

Reaction equation

HRID 67072 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:26]=[CH:27][C:28]=1[O:29][CH3:30])[C:6]([CH2:8][N:9]1[CH2:14][CH2:13][CH:12]([N:15]2[CH2:24][C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[NH:17][C:16]2=[O:25])[CH2:11][CH2:10]1)=[O:7].[BH4-].[Na+]>CO>[CH3:1][O:2][C:3]1[CH:4]=[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:26]=[CH:27][C:28]=1[O:29][CH3:30]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 127979841-(3,4-dimethoxybenzoylmethyl)-4-[3,4-dihydro-2(1H)-quinazolinon-3-yl]-piperidine

Product 1

HCID 127979861-[2-(3,4-Dimethoxyphenyl)-2-hydroxyethyl]-4-[3,4-dihydro-2(1H)-quinazolinon-3-yl]-piperidineYield 66.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In this example 2.80 g of 1-(3,4-dimethoxybenzoylmethyl)-4-[3,4-dihydro-2(1H)-quinazolinon-3-yl]-piperidine and 150 ml of methanol are mixed and stirred at room temperature. Then, 460 mg of sodium borohydride is added to the stirred mixture over a period of 30 minutes. Thereafter, 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 2.02 g of a crude product. The crude product is crystallized from hot ethanol to obtain 1.86 g of the desired product.

Workup

  1. stirringThereafter, 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 2.02 g of a crude product
  6. customThe crude product is crystallized from hot ethanol

Sources & evidence

ORD record
ord-5aa868eed3b24f508e8479e87dceebba
Source dataset
uspto-grants-1982_08
Patent number
US04344948

Reaction notes

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