Methylamine → 1-(4-chlorophenyl)-N-methylCyclopropanecarboxamide

HRID 1174663Notes

Reaction equation

HRID 1174663 reaction equation
CN.[CH2:3]([N:5](CC)CC)C.[Cl:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2([C:20](Cl)=[O:21])[CH2:19][CH2:18]2)=[CH:13][CH:12]=1>O1CCCC1.C(Cl)Cl>[Cl:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2([C:20]([NH:5][CH3:3])=[O:21])[CH2:19][CH2:18]2)=[CH:13][CH:12]=1

Participants

6

Reactant 3

HCID 6329MethylamineHCID 8471TriethylamineHCID 220161751-(4-Chlorophenyl)cyclopropane-1-carbonyl chloride

Product 1

HCID 227221451-(4-chlorophenyl)-N-methylCyclopropanecarboxamide

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

A solution of methylamine in tetrahydrofuran (THF) (2.0 M, 3.5 mL) was mixed with triethylamine (2.1 mL, 15 mmol). The resulting mixture was added to a solution of 1-(4-chlorophenyl)cyclopropanecarbonyl chloride in methylene chloride (15.0 mL) at 0° C. The resulting mixture was stirred at room temperature (about 25° C.) for 30 min, and was then quenched with saturated sodium bicarbonate (25 mL). The quenched mixture was extracted with ethyl acetate (3×40 mL). The combined ethyl acetate extracts were washed with brine, dried over Na2SO4, and filtered. The filtrate was concentrated under reduced pressure to provide the product, 1-(4-chlorophenyl)-N-methylcyclopropanecarboxamide, which was used in next step without further purification.

Workup

  1. customwas then quenched with saturated sodium bicarbonate (25 mL)
  2. extractionThe quenched mixture was extracted with ethyl acetate (3×40 mL)
  3. washThe combined ethyl acetate extracts were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-6524debad5684430a380f1a4df8f79c0
Source dataset
uspto-grants-2010_11
Patent number
US07838544B2

Reaction notes

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