Cyclopropylamine → N-Cyclopropyl-3-iodo-4-methylbenzamide
Reaction equation
[I:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[C:5]([OH:7])=O.CN(C(ON1N=NC2[CH:23]=[CH:24][CH:25]=[N:26]C1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C1C=CC2N(O)N=NC=2C=1.C1(N)CC1.CCN(C(C)C)C(C)C>CN(C=O)C>[CH:25]1([NH:26][C:5](=[O:7])[C:4]2[CH:8]=[CH:9][C:10]([CH3:11])=[C:2]([I:1])[CH:3]=2)[CH2:23][CH2:24]1Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Procedure
3-Iodo-4-methylbenzoic acid (5 g, 19.1 mmol) and HATU (8.71 g, 22.9 mmol) in DMF (25 ml) were stirred at room temperature for 10 minutes. HOBT (2.58 g, 19.1 mmol), cyclopropylamine (1.37 g, 22.9 mmol) and DIPEA (2.5 ml, 57.3 mmol) were added and stirring continued for 18 h. The DMF was evaporated under vacuum and the residue partitioned between DCM (100 ml) and aqueous sodium carbonate (1M, 75 ml). The aqueous layer was extracted with DCM (50 ml) and the combined organic phases washed with brine (75 ml) and dried (magnesium sulphate). The solution was absorbed onto silica and purified by chromatography on silica eluting with ethyl acetate/cyclohexane (1:3). The product fractions were reduced to dryness under vacuum to give N-cyclopropyl-3-iodo-4-methylbenzamide (4.7 g, 82%). LCMS: retention time 3.09 min, MH+302.
Workup
- customThe DMF was evaporated under vacuum
- customthe residue partitioned between DCM (100 ml) and aqueous sodium carbonate (1M, 75 ml)
- extractionThe aqueous layer was extracted with DCM (50 ml)
- washthe combined organic phases washed with brine (75 ml)
- dry with materialdried (magnesium sulphate)
- customThe solution was absorbed onto silica
- custompurified by chromatography on silica eluting with ethyl acetate/cyclohexane (1:3)
Sources & evidence
- ORD record
- ord-35818c7c2a9e4945bfe580756ae98843
- Source dataset
- uspto-grants-2008_07
- Patent number
- US07396843B2
Reaction notes
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