2,3-Dihydro-1,4-benzodioxin-6-carbaldehyde → Tert-butyl 4-((2,3-dihydro-1,4-benzodioxin-6-ylmethyl)amino)-4-methylpiperidine-1-carboxylate

HRID 39674

Reaction equation

HRID 39674 reaction equation
[NH2:1][C:2]1([CH3:15])[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.[O:16]1[C:21]2[CH:22]=[CH:23][C:24]([CH:26]=O)=[CH:25][C:20]=2[O:19][CH2:18][CH2:17]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl.C(O)(=O)C.ClCCl>[O:16]1[C:21]2[CH:22]=[CH:23][C:24]([CH2:26][NH:1][C:2]3([CH3:15])[CH2:3][CH2:4][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:6][CH2:7]3)=[CH:25][C:20]=2[O:19][CH2:18][CH2:17]1

Participants

8

Reactant 4

HCID 2481272,3-Dihydro-1,4-benzodioxin-6-carbaldehydeHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydride2×HCID 11310432tert-Butyl 4-amino-4-methylpiperidine-1-carboxylate

Product 1

HCID 59398035Tert-butyl 4-((2,3-dihydro-1,4-benzodioxin-6-ylmethyl)amino)-4-methylpiperidine-1-carboxylate

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

To 5 mL of a dichloromethane solution containing 0.50 g of tert-butyl 4-amino-4-methylpiperidine-1-carboxylate, 0.38 g of 2,3-dihydro-1,4-benzodioxin-6-carbaldehyde and 0.13 mL of acetic acid were added, and the mixture was stirred at room temperature for 3 hours. The reaction mixture was added with 0.74 g of sodium triacetoxyborohydride and stirred at the same temperature for 30 minutes. The reaction mixture was added with 0.74 g of sodium triacetoxyborohydride and stirred at the same temperature for 30 minutes, and then the reaction mixture was stirred for 1 hour under reflux by heating. Thereto were added chloroform and an aqueous saturated sodium hydrogen carbonate solution. The organic layer was separated, and the aqueous layer was extracted with chloroform. The organic layer and the extract were combined, and the resultant solution was washed with an aqueous saturated sodium chloride solution and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure to obtain 0.81 g of a light brown oily substance, tert-butyl 4-((2,3-dihydro-1,4-benzodioxin-6-ylmethyl)amino)-4-methylpiperidine-1-carboxylate.

Workup

  1. additionwere added
  2. stirringstirred at the same temperature for 30 minutes
  3. stirringstirred at the same temperature for 30 minutes
  4. stirringthe reaction mixture was stirred for 1 hour
  5. temperatureunder reflux
  6. temperatureby heating
  7. customThe organic layer was separated
  8. extractionthe aqueous layer was extracted with chloroform
  9. washthe resultant solution was washed with an aqueous saturated sodium chloride solution
  10. dry with materialdried over anhydrous magnesium sulfate
  11. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-c846f63164644d04a5a0217a7ae5a053
Source dataset
uspto-grants-2013_09
Patent number
US08524738B2

Linked notes

Loading…