Hydrochloric Acid → 1-{3-[2-(1-Benzothiophen-5-yl)ethoxy]propyl}-3-pyrrolidinamine

HRID 2386082Notes

Reaction equation

HRID 2386082 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][CH2:11][O:12][CH2:13][CH2:14][CH2:15][N:16]3[CH2:20][CH2:19][CH:18]([NH:21]C(=O)[O-])[CH2:17]3)=[CH:9][C:4]=2[CH:3]=[CH:2]1.Cl.O.[OH-].[Na+]>C(OCC)(=O)C>[S:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][CH2:11][O:12][CH2:13][CH2:14][CH2:15][N:16]3[CH2:20][CH2:19][CH:18]([NH2:21])[CH2:17]3)=[CH:9][C:4]=2[CH:3]=[CH:2]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 865973431-{3-[2-(1-Benzothiophen-5-yl)ethoxy]propyl}-3-pyrrolidinylcarbamate

Product 1

HCID 219900601-{3-[2-(1-Benzothiophen-5-yl)ethoxy]propyl}-3-pyrrolidinamine

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

In 7.0 mL of ethyl acetate was dissolved 1.12 g of tert-butyl=1-{3-[2-(1-benzothiophen-5-yl)ethoxy]propyl}-3-pyrrolidinylcarbamate, and 1.86 mL of 6 mol/L hydrochloric acid was added to the solution, after which the resulting mixture was heated under reflux for 1 hour. After the reaction mixture was cooled, water and ethyl acetate were added thereto and the pH was adjusted to 10 with a 2 mol/L aqueous sodium hydroxide solution, and the organic layer was separated. The organic layer was washed with water and then a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then distilled under reduced pressure to remove the solvent. The residue was purified by a column chromatography (eluent; chloroform:methanol=30:1 to 20:1) to obtain 0.38 g of 1-{3-[2-(1-benzothiophen-5-yl)ethoxy]propyl}-3-pyrrolidinamine as a light-yellow oil.

Workup

  1. additionwas added to the solution
  2. temperatureafter which the resulting mixture was heated
  3. temperatureunder reflux for 1 hour
  4. temperatureAfter the reaction mixture was cooled
  5. customthe organic layer was separated
  6. washThe organic layer was washed with water
  7. dry with materiala saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate
  8. distillationdistilled under reduced pressure
  9. customto remove the solvent
  10. customThe residue was purified by a column chromatography (eluent; chloroform:methanol=30:1 to 20:1)

Sources & evidence

ORD record
ord-def57bcbf060490f802ade0f0bddc3be
Source dataset
uspto-grants-2012_09
Patent number
USRE043676E1

Reaction notes

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