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

HRID 67058Notes

Reaction equation

HRID 67058 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[CH2:20][C:19]3[CH:21]=[CH:22][CH:23]=[CH:24][C:18]=3[O: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[CH2:20][C:19]4[CH:21]=[CH:22][CH:23]=[CH:24][C:18]=4[O: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 borohydride2×HCID 13037615HCID 13037615, compound

Product 1

HCID 130521671-[2-(3,4-Dimethoxyphenyl)-2-hydroxyethyl]-4-(2-oxo-3,4-dihydro-2H-1,3-benzoxazin-3-yl)-piperidineYield 83.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In this example, 3.0 g of 1-(3,4-dimethoxybenzoylmethyl)-4-(2-oxo-3,4-dihydro-2H-1,3-benzoxazin-3-yl)-piperidine obtained in Example 1 is mixed with 150 ml of methanol. While this mixture is stirred at 0°-10° C., 0.8 g of sodium borohydride is added thereto over a period of 3 hours. The reaction solution is stirred overnight at room temperature. Then, the solution 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 2.77 g of a crude product. The crude product is recrystallized from ethanol to obtain 2.52 g of the desired product.

Workup

  1. stirringThe reaction solution 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 2.77 g of a crude product
  7. customThe crude product is recrystallized from ethanol

Sources & evidence

ORD record
ord-a7052222cf7a489bb19b9f5bf2107f95
Source dataset
uspto-grants-1982_08
Patent number
US04344945

Reaction notes

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