Methylamine → HCID 67072284, compound

HRID 1242385Notes

Reaction equation

[CH2:1]([O:3][C:4]([C:6]([CH3:18])([O:8][C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][CH:17]=1)[C:12](O)=[O:13])[CH3:7])=[O:5])[CH3:2].CN.Cl.[CH3:22][N:23](C)CCCN=C=NCC>C(Cl)Cl.C(O)C.CN(C)C1C=CN=CC=1>[CH2:1]([O:3][C:4](=[O:5])[C:6]([CH3:18])([O:8][C:9]1[CH:17]=[CH:16][CH:15]=[C:11]([C:12](=[O:13])[NH:23][CH3:22])[CH:10]=1)[CH3:7])[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

1.0 g (4.0 mmol) of 3-(1-ethoxycarbonyl-1-methyl-ethoxy)-benzoic acid was dissolved in 50 ml of methylene chloride; then, 1.5 ml (4.0 mmol) of a methylamine-solution in ethanol was added. The reaction mixture was cooled down to 0° C. and 0.91 g (4.8 mmol) of N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride and 1.50 g (11.9 mmol) of 4-dimethylaminopyridine were added. After stirring for two hours at ambient temperature, it was poured into crashed ice/HCl (1N) and extracted twice with MeCl2. The combined organic phases were washed with water and brine and dried over anhydrous magnesium sulfate. After evaporation of the solvent, the crude product was purified by flash chromatography (SiO2, MeCl2/MeOH) to give 0.97 g of the title compound in form of colorless needles.

Workup

additionit was poured
extractionextracted twice with MeCl2
washThe combined organic phases were washed with water and brine
dry with materialdried over anhydrous magnesium sulfate
customAfter evaporation of the solvent
customthe crude product was purified by flash chromatography (SiO2, MeCl2/MeOH)

Sources & evidence

ORD record: ord-918ce0aa892f45af83668258dd9b956a
Source dataset: uspto-grants-2006_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07115611B2

Reaction notes

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