Water → HCID 23079686, compound

HRID 2112763Notes

Reaction equation

HRID 2112763 reaction equation
C([N:8]1[CH2:13][CH2:12][O:11][CH:10]([CH2:14][CH2:15][CH2:16][N:17]2[CH2:21][CH2:20][CH2:19][CH2:18]2)[CH2:9]1)C1C=CC=CC=1.C(N(CC)CC)C.[Cl:29]C(OC(Cl)C)=O.O>ClCCCl>[ClH:29].[N:17]1([CH2:16][CH2:15][CH2:14][CH:10]2[O:11][CH2:12][CH2:13][NH:8][CH2:9]2)[CH2:18][CH2:19][CH2:20][CH2:21]1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 5213051-Chloroethyl chloroformateHCID 23079685HCID 23079685, compound

Product 1

HCID 23079686HCID 23079686, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Procedure

4-Benzyl-2-(3-pyrrolidin-1-yl-propyl)morpholine (180 mg, 0.62 mmol) prepared according to Process Step 1 was dissolved in 1,2-dichloroethane (5 mL), and the solution was mixed with triethylamine (0.086 mL, 0.62 mmol) and 1-chloroethyl chloroformate (0.20 mL, 1.87 mmol), followed by stirring under reflux for three hours. The reaction mixture was cooled and was mixed with 1,2-dichloroethane (50 mL) and water (50 mL), followed by separation. The organic layer was washed with brine (50 mL), was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was dissolved in methanol (5 mL), followed by stirring under reflux for one hour. After distilling off the solvent under reduced pressure, diethyl ether (5 mL) was added for crystallization, and the precipitated crystals were collected by filtration. The crystals were dried under reduced pressure and thereby yielded 2-(3-pyrrolidin-1-ylpropyl)morpholine hydrochloride (135 mg, in a yield of 93%).

Workup

  1. temperatureunder reflux for three hours
  2. temperatureThe reaction mixture was cooled
  3. customfollowed by separation
  4. washThe organic layer was washed with brine (50 mL)
  5. dry with materialwas dried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. dissolutionThe residue was dissolved in methanol (5 mL)
  8. stirringby stirring
  9. temperatureunder reflux for one hour
  10. distillationAfter distilling off the solvent under reduced pressure, diethyl ether (5 mL)
  11. additionwas added for crystallization
  12. filtrationthe precipitated crystals were collected by filtration
  13. customThe crystals were dried under reduced pressure

Sources & evidence

ORD record
ord-ed7d222f98e643dabaa1ebba2180947b
Source dataset
uspto-grants-2009_04
Patent number
US07524852B2

Reaction notes

Loading…