Sodium Bicarbonate → HCID 23153143, compound

HRID 1631979Notes

Reaction equation

HRID 1631979 reaction equation
Cl.[CH2:2]([N:9]([CH2:13][CH2:14]Cl)[CH2:10][CH2:11]Cl)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[NH2:16][CH:17]1[CH2:20][N:19]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:18]1.C(=O)(O)[O-].[Na+]>C(O)C>[CH2:2]([N:9]1[CH2:13][CH2:14][N:16]([CH:17]2[CH2:18][N:19]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:20]2)[CH2:11][CH2:10]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 1516507Tert-butyl 3-aminoazetidine-1-carboxylateHCID 2777881N,N-Bis(2-chloroethyl)benzylamine hydrochloride

Product 1

HCID 23153143HCID 23153143, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

6.33 g (29.0 mmol) of benzylbis(2-chloroethyl)amine hydrochloride were dissolved in ethanol (100 ml) and, while stirring, 5.00 g (29.0 mmol) of tert-butyl 3-aminoazetidine-1-carboxylate and 9.76 g (116 mmol) of sodium bicarbonate were added. The resulting reaction solution was heated under reflux for 4 h. The cooled reaction mixture was concentrated in vacuo, 100 ml of water were added and the aqueous phase was extracted with ethyl acetate (4×60 ml). The combined organic phases were washed with saturated aqueous NaHCO3 solution, dried over magnesium sulfate and concentrated in vacuo. The residue was purified by chromatography on silica gel (mobile phase gradient 2.5-5% methanol in dichloromethane). Yield: 6.27 g (65%) of yellow oil

Workup

  1. customThe resulting reaction solution
  2. temperaturewas heated
  3. temperatureunder reflux for 4 h
  4. customThe cooled reaction mixture
  5. concentrationwas concentrated in vacuo, 100 ml of water
  6. additionwere added
  7. extractionthe aqueous phase was extracted with ethyl acetate (4×60 ml)
  8. washThe combined organic phases were washed with saturated aqueous NaHCO3 solution
  9. dry with materialdried over magnesium sulfate
  10. concentrationconcentrated in vacuo
  11. customThe residue was purified by chromatography on silica gel (mobile phase gradient 2.5-5% methanol in dichloromethane)

Sources & evidence

ORD record
ord-79f4230bc9e7410da28b7aa505d401d4
Source dataset
uspto-grants-2014_07
Patent number
US08791148B2

Reaction notes

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