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

HRID 67074Notes

Reaction equation

HRID 67074 reaction equation
[CH2:1]1[O:29][C:28]2[CH:27]=[CH:26][C:5]([C:6]([CH2:8][N:9]3[CH2:14][CH2:13][CH:12]([N:15]4[C:24]5[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=5)[CH2:18][NH:17][C:16]4=[O:25])[CH2:11][CH2:10]3)=[O:7])=[CH:4][C:3]=2[O:2]1.[BH4-].[Na+]>CO>[CH2:1]1[O:29][C:28]2[CH:27]=[CH:26][C:5]([CH:6]([OH:7])[CH2:8][N:9]3[CH2:14][CH2:13][CH:12]([N:15]4[C:24]5[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=5)[CH2:18][NH:17][C:16]4=[O:25])[CH2:11][CH2:10]3)=[CH:4][C:3]=2[O:2]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 127979971-(3,4-methylenedioxybenzoylmethyl)-4-[3,4-dihydro-2(1H)-quinazolinon-1-yl]-piperidine

Product 1

HCID 127979991-[2-(3,4-Methylenedioxyphenyl)-2-hydroxyethyl]-4-[3,4-dihydro-2(1H)-quinazolinon-1-yl]-piperidineYield 64.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In this example, 2.70 g of 1-(3,4-methylenedioxybenzoylmethyl)-4-[3,4-dihydro-2(1H)-quinazolinon-1-yl]-piperidine and 150 ml of methanol are mixed and stirred under ice-cooling. Then, 2.0 g of sodium borohydride is added to the stirred mixture over a period of one hour. Subsequently, the mixture is brought back to room temperature and stirred for 3 hours at room temperature and the reaction solution is concentrated. The resultant residue is mixed with 50 ml of water and the mixture is extracted with ethyl acetate (100 ml×2 and 50 ml×1). The extract is washed with water, dried and concentrated. The resultant viscous residue is mixed with 5 ml of methanol. The crystals deposited are separated by filtration, washed with methanol and dried to obtain 2.05 g of a crude product. The crude product is recrystallized from hot ethanol to obtain 1.74 g of the desired product.

Workup

  1. temperaturecooling
  2. customis brought back to room temperature
  3. stirringstirred for 3 hours at room temperature
  4. concentrationthe reaction solution is concentrated
  5. additionThe resultant residue is mixed with 50 ml of water
  6. extractionthe mixture is extracted with ethyl acetate (100 ml×2 and 50 ml×1)
  7. washThe extract is washed with water
  8. customdried
  9. concentrationconcentrated
  10. additionThe resultant viscous residue is mixed with 5 ml of methanol
  11. customThe crystals deposited are separated by filtration
  12. washwashed with methanol
  13. customdried
  14. customto obtain 2.05 g of a crude product
  15. customThe crude product is recrystallized from hot ethanol

Sources & evidence

ORD record
ord-491ecc13577d476f88fc19bf72a357c8
Source dataset
uspto-grants-1982_08
Patent number
US04344948

Reaction notes

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