Sodium Carbonate → HCID 69053505, compound

HRID 1264648Notes

Reaction equation

HRID 1264648 reaction equation
Br[CH2:2][CH2:3][CH:4]1[O:8][CH2:7][CH2:6][O:5]1.[C:9]1([CH2:15][NH:16][CH2:17][C@@H:18]2[CH2:23][CH2:22][NH:21][CH2:20][C@H:19]2[OH:24])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C([O-])([O-])=O.[Na+].[Na+]>>[O:5]1[CH2:6][CH2:7][O:8][CH:4]1[CH2:3][CH2:2][N:21]1[CH2:22][CH2:23][C@@H:18]([CH2:17][NH:16][CH2:15][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C@H:19]([OH:24])[CH2:20]1

Participants

4

Reactant 3

HCID 10340Sodium CarbonateHCID 877762-(2-Bromoethyl)-1,3-dioxolaneHCID 69055364HCID 69055364, compound

Product 1

HCID 69053505HCID 69053505, compoundYield 46.8%

Procedure

A mixture of 2-(2-bromoethyl)-1,3-dioxolane (0.04 mol), intermediate (6) (0.04 mol) and Na2CO3 (10%, 0.08 mol) in MIK (400 ml) was stirred and refluxed for 20 hours and then cooled. The solvent was evaporated. The residue was taken up in DCM and water. The organic layer was separated, dried, filtered and the solvent was evaporated. The residue was purified by column chromatography over silica gel (eluent: CH2C2/(CH3OH/NH3) 96/4). The pure fractions were collected and the solvent was evaporated. Toluene was added and evaporated again, yielding 6 g of (trans)-1-[2-(1,3-dioxolan-2-yl)ethyl]-4-[[(phenylmethyl)amino]methyl]-3-piperidinol (intermediate 7).

Workup

  1. temperaturerefluxed for 20 hours
  2. temperaturecooled
  3. customThe solvent was evaporated
  4. customThe organic layer was separated
  5. customdried
  6. filtrationfiltered
  7. customthe solvent was evaporated
  8. customThe residue was purified by column chromatography over silica gel (eluent: CH2C2/(CH3OH/NH3) 96/4)
  9. customThe pure fractions were collected
  10. customthe solvent was evaporated
  11. additionToluene was added
  12. customevaporated again

Sources & evidence

ORD record
ord-8b83838dd4764d34b12d539b3f614074
Source dataset
uspto-grants-2003_04
Patent number
US06544997B1

Reaction notes

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