Diisopropylethylamine → 3-methoxy-N-[(3R)-1-methylpyrrolidin-3-yl]-4-nitro-benzamide

HRID 2234458Notes

Reaction equation

HRID 2234458 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[N+:12]([O-:14])=[O:13])[C:6](Cl)=[O:7].C(N(CC)C(C)C)(C)C.Cl.Cl.[CH3:26][N:27]1[CH2:31][CH2:30][C@@H:29]([NH2:32])[CH2:28]1>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[N+:12]([O-:14])=[O:13])[C:6]([NH:32][C@@H:29]1[CH2:30][CH2:31][N:27]([CH3:26])[CH2:28]1)=[O:7]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 111276553-methoxy-4-nitro-benzoyl Chloride2×HCID 53256048(3R)-1-Methyl-3-PyrrolidinaMine hydrochloride2×

Product 1

HCID 686830363-methoxy-N-[(3R)-1-methylpyrrolidin-3-yl]-4-nitro-benzamideYield 47%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

3-methoxy-4-nitro-benzoyl chloride (Intermediate 189; 374 mg, 1.73 mmol) was dissolved in DCM (20 mL) and N,N-diisopropylethylamine (0.96 mL, 5.54 mmol) added. The mixture was cooled in an ice/water bath and (3R)-1-methylpyrrolidin-3-amine dihydrochloride (Intermediate 184; 300 mg, 1.73 mmol) in DCM (10 mL) added dropwise. The mixture was allowed to warm to room temperature and stirred for 0.5 hour. The mixture was washed with brine, 2N NaOH(aq), dried with MgSO4 and evaporated to yield the title compound as a brown solid (227 mg, 46.9%).

Workup

  1. temperatureThe mixture was cooled in an ice/water bath
  2. washThe mixture was washed with brine, 2N NaOH(aq)
  3. dry with materialdried with MgSO4
  4. customevaporated

Sources & evidence

ORD record
ord-ceb02e1255be4dd89cc2316532daad46
Source dataset
uspto-grants-2010_05
Patent number
US07709471B2

Reaction notes

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