Cyclopropylamine → HCID 178491237, compound

HRID 732106Notes

Reaction equation

HRID 732106 reaction equation
Cl.C(O[C:5](=[NH:14])[C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[CH:8][CH:7]=1)C.[CH:15]1([NH2:18])[CH2:17][CH2:16]1>C(Cl)Cl>[CH:15]1([NH:18][C:5](=[NH:14])[C:6]2[CH:7]=[CH:8][C:9]([O:12][CH3:13])=[CH:10][CH:11]=2)[CH2:17][CH2:16]1

Participants

4

Reactant 2

HCID 69828CyclopropylamineHCID 12270046Ethyl 4-methoxybenzimidate hydrochloride

Product 1

HCID 178491237HCID 178491237, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-methoxy-benzimidic acid ethyl ester hydrochloride (1.25 g, 5.8 mmol), DCM (5 ml) and cyclopropylamine (0.92 ml, 13.3 mmol) were mixed. After stirring at r.t for 3 h, the reaction mixture was concentrated in-vacuo. The residue was treated with cold aq. sodium hydroxide (1M) and extracted with EA. The combined organic phase was washed with water and brine, dried (Na2SO4), filtered and concentrated in-vacuo, to isolate the title compound (0.90 g, 82%). 1H-NMR: 7.64 (d, 2H), 6.90 (d, 2H), 5.3 (bs, 2H), 3.85 (s, 3H), 2.59 (m, 1H), 0.84 (m, 2H), 0.62 (m, 2H).

Workup

  1. concentrationthe reaction mixture was concentrated in-vacuo
  2. additionThe residue was treated with cold aq. sodium hydroxide (1M)
  3. extractionextracted with EA
  4. washThe combined organic phase was washed with water and brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in-vacuo

Sources & evidence

ORD record
ord-7fad59dcafca4665b83f4718518a4c68
Source dataset
uspto-grants-2009_09
Patent number
US07585881B2

Reaction notes

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