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

HRID 513259Notes

Reaction equation

HRID 513259 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-])=O)=[CH:4][C:3]=1[N:11]=[C:12]=[O:13].[NH:14]1[CH2:18][CH2:17][CH2:16][CH2:15]1>C(Cl)Cl>[NH2:8][C:5]1[CH:6]=[CH:7][C:2]([F:1])=[C:3]([NH:11][C:12]([N:14]2[CH2:18][CH2:17][CH2:16][CH2:15]2)=[O:13])[CH:4]=1

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 1443072-Fluoro-5-nitrophenyl isocyanate

Product 1

HCID 66841440N-(5-amino-2-fluorophenyl)pyrrolidine-1-carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 1-fluoro-2-isocyanato-4-nitrobenzene (1.125 g, 6.18 mmol) and pyrrolidine (485 mg, 6.8 mmol) in DCM (20 mL) was stirred at rt for 14 hrs. After concentrated, the mixture was extracted with ethyl acetate. The organic layer was washed with aqueous citric acid solution and dried over MgSO4, followed by hydrogenation with Pd/C (wet, 10%, 0.15 g) under a hydrogen balloon overnight. After filtration and concentration, the reasonable pure N-(5-amino-2-fluorophenyl)pyrrolidine-1-carboxamide (28.5, 1.44 g) was used for the next reactions. MS+: 224.2, UV: λ=271.6 nm. 1H NMR: (DMSO) δ7.44 (s, 1H), δ6.78 (m, 1H), δ6.20 (m, 1H), δ3.32 (m, 4H), δ1.83 (m, 4H).

Workup

  1. concentrationAfter concentrated
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with aqueous citric acid solution
  4. dry with materialdried over MgSO4
  5. customballoon overnight
  6. filtrationAfter filtration and concentration

Sources & evidence

ORD record
ord-a1a0bd20ba504e9eaf76cd3123f615c8
Source dataset
uspto-grants-2015_08
Patent number
US09102625B2

Reaction notes

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