1-Pyrrolidineethanamine → HCID 57917356, compound

HRID 69143Notes

Reaction equation

HRID 69143 reaction equation
[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[C:6](F)[CH:5]=1.[N:15]1([CH2:20][CH2:21][NH2:22])[CH2:19][CH2:18][CH2:17][CH2:16]1>CO.CCOC(C)=O>[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[C:6]([NH:22][CH2:21][CH2:20][N:15]2[CH2:19][CH2:18][CH2:17][CH2:16]2)[CH:5]=1

Participants

5

Reactant 2

HCID 13441-PyrrolidineethanamineHCID 592761Methyl 3-fluoro-4-nitrobenzoate

Product 1

HCID 57917356HCID 57917356, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-Fluoro-4-nitro-benzoic acid methyl ester (xiv) (1.08 g, 5.41 mmol) and 2-pyrrolidin-1-yl-ethylamine (1.36 g, 11.9 mmol) in MeOH (19 mL) were stirred under microwave irradiation at 100° C. for 10 min. The RM was diluted with EtOAc and washed with aqueous saturated NaHCO3 and brine, dried over Na2SO4, filtered and evaporated to dryness. The residue was dry loaded on silica gel and purified by chromatography with DCM and MeOH to yield the title product as an orange solid (tR 2.45 min (conditions 8), MH+=294).

Workup

  1. washwashed with aqueous saturated NaHCO3 and brine
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. customevaporated to dryness
  5. customThe residue was dry
  6. custompurified by chromatography with DCM and MeOH

Sources & evidence

ORD record
ord-8472042b9cbc48dfa57f8264ecf5bfbc
Source dataset
uspto-grants-2014_09
Patent number
US08822468B2

Reaction notes

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