Sodium borohydride → 1-[2-(3,4-dimethoxyphenyl)-2-hydroxyethyl]-4-(3,4-dihydro-2,2-dioxo-1H-2,1,3-benzothiadiazin-3-yl)-piperidine

HRID 67062Notes

Reaction equation

HRID 67062 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]([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[NH:17][S:16]2(=[O:26])=[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[NH:17][S:16]3(=[O:25])=[O:26])[CH2:13][CH2:14]2)[CH:27]=[CH:28][C:29]=1[O:30][CH3:31]

Participants

4

Reactant 2

HCID 4311764Sodium borohydride2×HCID 130521741-(3,4-dimethoxybenzoylmethyl)-4-(3,4-dihydro-2,2-dioxo-1H-2,1,3-benzothiadiazin-3-yl)-piperidine

Product 1

HCID 130521751-[2-(3,4-dimethoxyphenyl)-2-hydroxyethyl]-4-(3,4-dihydro-2,2-dioxo-1H-2,1,3-benzothiadiazin-3-yl)-piperidineYield 65.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In 150 ml of methanol, 2.2 g of 1-(3,4-dimethoxybenzoylmethyl)-4-(3,4-dihydro-2,2-dioxo-1H-2,1,3-benzothiadiazin-3-yl)-piperidine is suspended. While this suspension is stirred at room temperature, 1.0 g of sodium borohydride is added thereto by portions over a period of four hours. The mixture is stirred overnight at room temperature and 400 mg of sodium borohydride is added thereto. Then, the mixture is stirred overnight. The reaction solution is concentrated under reduced pressure. The residue is mixed with 100 ml of water and adjusted to pH 9.3 with concentrated hydrochloric acid. The resultant mixture is extracted with chloroform. The organic layer is washed with water, dried and freed from the solvent by distillation to obtain a syrup as a residue. This residue is crystallized by adding methanol thereto. The crystals are separated by filtration to obtain 1.93 g of crude crystals. The crude crystals are recrystallized from ethanol to obtain 1.45 g of 1-[2-(3,4-dimethoxyphenyl)-2-hydroxyethyl]-4-(3,4-dihydro-2,2-dioxo-1H-2,1,3-benzothiadiazin- 3-yl)-piperidine (Compound No. 10).

Workup

  1. stirringThe mixture is stirred overnight at room temperature
  2. stirringThen, the mixture is stirred overnight
  3. concentrationThe reaction solution is concentrated under reduced pressure
  4. additionThe residue is mixed with 100 ml of water
  5. extractionThe resultant mixture is extracted with chloroform
  6. washThe organic layer is washed with water
  7. customdried
  8. distillationfreed from the solvent by distillation
  9. customto obtain a syrup as a residue
  10. customThis residue is crystallized
  11. additionby adding methanol
  12. customThe crystals are separated by filtration
  13. customto obtain 1.93 g of crude crystals
  14. customThe crude crystals are recrystallized from ethanol

Sources & evidence

ORD record
ord-34483f0583a043d89978cc93c222940d
Source dataset
uspto-grants-1982_08
Patent number
US04344945

Reaction notes

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