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

HRID 67059Notes

Reaction equation

HRID 67059 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[CH2:20][C:19]5[CH:21]=[CH:22][CH:23]=[CH:24][C:18]=5[O: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[CH2:20][C:19]5[CH:21]=[CH:22][CH:23]=[CH:24][C:18]=5[O: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 borohydride2×HCID 130521661-(3,4-Methylenedioxybenzoylmethyl)-4-(2-oxo-3,4-dihydro-2H-1,3-benzoxazin-3-yl)-piperidine

Product 1

HCID 130521681-[2-(3,4-Methylenedioxyphenyl)-2-hydroxyethyl]-4-(2-oxo-3,4-dihydro-2H-1,3-benzoxazin-3-yl)-piperidineYield 82.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In this example, 3.0 g of 1-(3,4-methylenedioxybenzoylmethyl)-4-(2-oxo-3,4-dihydro-2H-1,3-benzoxazin-3-yl)-piperidine obtained in Example 2 is mixed with 150 ml of methanol. While the mixture is stirred at 0° to 10° C., 0.8 g of sodium borohydride is added thereto over a period of 3 hours. Then, the mixture is stirred overnight at room temperature. The mixture is further mixed with 0.4 g of sodium borohydride and stirred at room temperature for 3 hours. The white crystals deposited are separated by filtration, washed with methanol and water and dried to obtain 2.36 g of a crude product. In the meantime, the filtrate is concentrated under reduced pressure. The residue is mixed with water. The crystals deposited are separated by filtration, washed with water and dried to obtain 0.37 g of a crude product. The two crude products are combined and recrystallized from ethanol to obtain 2.49 g of the desired product.

Workup

  1. stirringThen, the mixture is stirred overnight at room temperature
  2. stirringstirred at room temperature for 3 hours
  3. customThe white crystals deposited are separated by filtration
  4. washwashed with methanol and water
  5. customdried
  6. customto obtain 2.36 g of a crude product
  7. concentrationIn the meantime, the filtrate is concentrated under reduced pressure
  8. additionThe residue is mixed with water
  9. customThe crystals deposited are separated by filtration
  10. washwashed with water
  11. customdried
  12. customto obtain 0.37 g of a crude product
  13. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-743755c93bf24ce68b7f0d95b7920496
Source dataset
uspto-grants-1982_08
Patent number
US04344945

Reaction notes

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