Sodium Hydroxide → HCID 23138364, compound

HRID 1162338Notes

Reaction equation

HRID 1162338 reaction equation
O=[C:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.Cl.Cl.[NH2:17][CH2:18][CH2:19][C:20]1[N:24]=[CH:23][NH:22][CH:21]=1.[C:25](O[BH-](OC(=O)C)OC(=O)C)(=[O:27])C.[Na+].[OH-].[Na+]>ClCCCl>[O:27]=[C:25]1[N:24]2[CH:23]=[N:22][CH:21]=[C:20]2[CH2:19][CH2:18][N:17]1[CH:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 5049666Sodium triacetoxyborohydrideHCID 178478691HCID 178478691, compound

Product 1

HCID 23138364HCID 23138364, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of tert-butyl 4-oxo-1-piperidinecarboxylate (11 g) and histamine dihydrochloride (10 g) in 1,2-dichloroethane (300 ml) was added sodium triacetoxyborohydride (17 g), and mixed at room temperature for 15 hours. pH of the aqueous layer was adjusted to about 12 by adding a 1 N aqueous sodium hydroxide solution to the reaction solution, and then extracted with chloroform. The extract was dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure. The resulting yellow oil was dissolved in dichloromethane (300 ml), DBU (13 ml) and N,N′-carbonyldiimidazole (7.6 g) were added to the reaction solution, and mixed at room temperature for 15 hours. The reaction mixture was diluted with water and chloroform, and the organic layer was collected by separation, and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified with silica gel column (ethyl acetate:ethanol=5:1) to obtain the title compound as a colorless oil (13 g, 77%).

Workup

  1. additionmixed at room temperature for 15 hours
  2. extractionextracted with chloroform
  3. dry with materialThe extract was dried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. dissolutionThe resulting yellow oil was dissolved in dichloromethane (300 ml)
  6. additionDBU (13 ml) and N,N′-carbonyldiimidazole (7.6 g) were added to the reaction solution
  7. additionmixed at room temperature for 15 hours
  8. additionThe reaction mixture was diluted with water and chloroform
  9. customthe organic layer was collected by separation
  10. dry with materialdried over anhydrous magnesium sulfate
  11. distillationThe solvent was distilled off under reduced pressure
  12. customthe residue was purified with silica gel column (ethyl acetate:ethanol=5:1)

Sources & evidence

ORD record
ord-b3d30c33f028478cace0a82f42c2bb5f
Source dataset
uspto-grants-2010_10
Patent number
US07820673B2

Reaction notes

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