Tert-butyl (1-benzylpiperidin-4-yl)(2,3-dihydro-(1,4)dioxino(2,3-c)pyridin-7-yl methyl)carbamate → Tert-butyl (2,3-dihydro(1,4)dioxino(2,3-c)pyridin-7-ylmethyl)(piperidin-4-yl)carbamate monohydrate

HRID 1804728Notes

Reaction equation

HRID 1804728 reaction equation
C([N:8]1[CH2:13][CH2:12][CH:11]([N:14]([CH2:22][C:23]2[N:28]=[CH:27][C:26]3[O:29][CH2:30][CH2:31][O:32][C:25]=3[CH:24]=2)[C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH2:10][CH2:9]1)C1C=CC=CC=1>CO.[C].[Pd]>[OH2:16].[O:32]1[C:25]2[CH:24]=[C:23]([CH2:22][N:14]([CH:11]3[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]3)[C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[N:28]=[CH:27][C:26]=2[O:29][CH2:30][CH2:31]1

Participants

4

Reactant 1

HCID 70846775Tert-butyl (1-benzylpiperidin-4-yl)(2,3-dihydro-(1,4)dioxino(2,3-c)pyridin-7-yl methyl)carbamate

Product 1

HCID 86646182Tert-butyl (2,3-dihydro(1,4)dioxino(2,3-c)pyridin-7-ylmethyl)(piperidin-4-yl)carbamate monohydrateYield 121.7%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 5.9 g of tert-butyl (1-benzylpiperidin-4-yl)(2,3-dihydro-(1,4)dioxino(2,3-c)pyridin-7-yl methyl)carbamate in 30 mL of methanol, 1.2 g of 5% palladium carbon was added, and the mixture was stirred for 7 hours at 60° C. under a hydrogen atmosphere. The mixture was subjected to celite filtration, and 40 mL of ethyl acetate and 30 mL of a 0.5 mol/L sodium hydroxide aqueous solution were added to the filtrate. The organic layer was washed with saturated sodium chloride solution, dried using sodium sulfate and the solvent was evaporated under reduced pressure. The obtained residue was recrystallized from 5 mL of ethyl acetate-15 mL of heptane to give 3.0 g of tert-butyl ((2,3-dihydro-(1,4)dioxino(2,3-c)pyridin-7-yl)methyl)(piperidin-4-yl)carbamate monohydrate as a white powder.

Workup

  1. filtrationThe mixture was subjected to celite filtration, and 40 mL of ethyl acetate and 30 mL of a 0.5 mol/L sodium hydroxide aqueous solution
  2. additionwere added to the filtrate
  3. washThe organic layer was washed with saturated sodium chloride solution
  4. customdried
  5. customthe solvent was evaporated under reduced pressure
  6. customThe obtained residue was recrystallized from 5 mL of ethyl acetate-15 mL of heptane

Sources & evidence

ORD record
ord-f19f8f1da26f4f4480677d38630737bd
Source dataset
uspto-grants-2013_01
Patent number
US08354426B2

Reaction notes

Loading…