Pyrrolidine → N-(2-amino-5-bromophenyl)pyrrolidine-1-carboxamide

HRID 2201706Notes

Reaction equation

HRID 2201706 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-])=O)=[C:6]([CH:8]=1)[NH2:7].ClC(Cl)(O[C:16](=[O:22])OC(Cl)(Cl)Cl)Cl.[NH:24]1[CH2:28][CH2:27][CH2:26][CH2:25]1>ClCCl>[NH2:9][C:5]1[CH:4]=[CH:3][C:2]([Br:1])=[CH:8][C:6]=1[NH:7][C:16]([N:24]1[CH2:28][CH2:27][CH2:26][CH2:25]1)=[O:22]

Participants

5

Reactant 3

HCID 31268PyrrolidineHCID 94429TriphosgeneHCID 53147665-Bromo-2-nitroaniline

Product 1

HCID 86712537N-(2-amino-5-bromophenyl)pyrrolidine-1-carboxamideYield 34.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 5-bromo-2-nitroaniline (1 g, 4.61 mmol) in dichloromethane (15 mL) were added TEA (8.35 mL, 59.9 mmol, 1.3 eq.) and triphosgene (1.37 g, 4.61 mmol, 1 equiv.) at 0° C. The mixture was stirred for three hours at room temperature and the pyrrolidine (0.39 g, 5.53 mmol, 1.2 equiv.) was added slowly. The reaction was stirred for an additional two hours. The reaction crude was diluted with dichloromethane and washed with water and brine. The organic layers were dried over MgSO4, filtered and evaporated. The residue was purified by column chromatography on eluting ethyl acetate and hexane to allow N-(2-amino-5-bromophenyl)pyrrolidine-1-carboxamide (0.45 g, 31% yield).

Workup

  1. stirringThe reaction was stirred for an additional two hours
  2. customThe reaction crude
  3. washwashed with water and brine
  4. dry with materialThe organic layers were dried over MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by column chromatography
  8. washon eluting ethyl acetate and hexane

Sources & evidence

ORD record
ord-7442e606967c4d3786e9a5b7970a3244
Source dataset
uspto-grants-2016_06
Patent number
US09365498B2

Reaction notes

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