Sodium borohydride → HCID 13052170, compound

HRID 67060Notes

Reaction equation

HRID 67060 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:27]=[CH:28][C:29]=1[O:30][CH3:31])[C:6]([CH:8]([N:10]1[CH2:15][CH2:14][CH:13]([N:16]2[CH2:21][C:20]3[CH:22]=[CH:23][CH:24]=[CH:25][C:19]=3[O:18][C:17]2=[O:26])[CH2:12][CH2:11]1)[CH3:9])=[O:7].[BH4-].[Na+]>CO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:6]([OH:7])[CH:8]([N:10]2[CH2:11][CH2:12][CH:13]([N:16]3[CH2:21][C:20]4[CH:22]=[CH:23][CH:24]=[CH:25][C:19]=4[O:18][C:17]3=[O:26])[CH2:14][CH2:15]2)[CH3:9])[CH:27]=[CH:28][C:29]=1[O:30][CH3:31]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 130521691-[1-(3,4-Dimethoxybenzoyl)-ethyl]-4-(2-oxo-3,4-dihydro-2H-1,3-benzoxazin-3-yl)-piperidine

Product 1

HCID 13052170HCID 13052170, compoundYield 59.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In this example, 2.8 g of 1-[1-(3,4-dimethoxybenzoyl)-ethyl]-4-(2-oxo-3,4-dihydro-2H-1,3-benzoxazin-3-yl)-piperidine obtained in Example 5 is mixed with 150 ml of methanol. While the mixture is stirred at 0° to 10° C., 2 g of sodium borohydride is added thereto over a period of one hour. The mixture is further stirred for 3 hours at the same temperature and then stirred overnight at room temperature. The white crystals deposited are separated by filtration, washed with methanol and water and dried to obtain 1.90 g of a crude product. The crude product is recrystallized from ethanol to obtain 1.67 g of the desired product.

Workup

  1. stirringThe mixture is further stirred for 3 hours at the same temperature
  2. stirringstirred overnight at room temperature
  3. customThe white crystals deposited are separated by filtration
  4. washwashed with methanol and water
  5. customdried
  6. customto obtain 1.90 g of a crude product
  7. customThe crude product is recrystallized from ethanol

Sources & evidence

ORD record
ord-8713c571933e45a190eb9355e1dd19b7
Source dataset
uspto-grants-1982_08
Patent number
US04344945

Reaction notes

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