Acetic Acid → HCID 66657264, compound

HRID 660118Notes

Reaction equation

HRID 660118 reaction equation
C(O)(=O)C.C(OC([N:12]1[CH2:16][CH2:15][C:14](=O)[CH2:13]1)=O)(C)(C)C.[Cl:18][C:19]1[CH:20]=[C:21]([NH:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:22]=[CH:23][C:24]=1[Cl:25].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[ClH:18].[ClH:18].[Cl:18][C:19]1[CH:20]=[C:21]([N:26]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:14]2[CH2:15][CH2:16][NH:12][CH2:13]2)[CH:22]=[CH:23][C:24]=1[Cl:25]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 471360Tert-butyl 3-oxopyrrolidine-1-carboxylateHCID 3027195HCID 3027195, compoundHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 66657264HCID 66657264, compoundYield 10%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

An acetic acid solution (15 ml) containing 3-oxopyrrolidine-1-carboxylic acid tert-butyl ester (0.67 g) and (3,4-dichlorophenyl)phenylamine (0.94 g) was stirred at room temperature over night. To the mixture was added 1.5 g of sodium triacetoxyborohydride, followed by stirring at room temperature for 8 hours. Dichloromethane was added to the reaction solution and washed with water, followed by drying over magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was then purified by silica gel column chromatography (n-hexane:ethyl acetate=20:1). The solvent was distilled off from the purified product under reduced pressure, and the residue was dissolved in 1 N hydrochloric acid-ethanol and heated under reflux for one hour. The reaction solution was concentrated to dryness to thereby obtain 50 mg of brown amorphous solid (3,4-dichlorophenyl)phenylpyrrolidin-3-ylamine dihydrochloride.

Workup

  1. stirringby stirring at room temperature for 8 hours
  2. washwashed with water
  3. dry with materialby drying over magnesium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customthe residue was then purified by silica gel column chromatography (n-hexane:ethyl acetate=20:1)
  6. distillationThe solvent was distilled off from the purified product under reduced pressure
  7. dissolutionthe residue was dissolved in 1 N hydrochloric acid-ethanol
  8. temperatureheated
  9. temperatureunder reflux for one hour
  10. concentrationThe reaction solution was concentrated to dryness

Sources & evidence

ORD record
ord-4d1636fecc564e1d86821b519eca73fb
Source dataset
uspto-grants-2011_12
Patent number
US08084442B2

Reaction notes

Loading…