Acetic Acid → HCID 66657264, compound

HRID 1966036Notes

Reaction equation

HRID 1966036 reaction equation
C(O)(=O)C.O=[C:6]1[CH2:10][CH2:9][N:8](C(O)=O)[CH2:7]1.[Cl:14][C:15]1[CH:16]=[C:17]([NH:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:18]=[CH:19][C:20]=1[Cl:21].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[ClH:14].[ClH:14].[Cl:14][C:15]1[CH:16]=[C:17]([N:22]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:6]2[CH2:10][CH2:9][NH:8][CH2:7]2)[CH:18]=[CH:19][C:20]=1[Cl:21]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 3027195HCID 3027195, compoundHCID 5049666Sodium triacetoxyborohydrideHCID 21925648HCID 21925648, compound

Product 1

HCID 66657264HCID 66657264, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

An acetic acid solution (15 ml) containing 3-oxopyrrolidine-1-carboxylic acid text-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-b34b8075cf5c4ea7882094ac35fb65a6
Source dataset
uspto-grants-2013_04
Patent number
US08420623B2

Reaction notes

Loading…