Hydrochloric Acid → N-{2-[4-(1-methylprop-1-yloxy)-phenoxy]-ethyl}-cyclopropanecarboxamide

HRID 1087808Notes

Reaction equation

HRID 1087808 reaction equation
[CH:1]1([C:4](Cl)=[O:5])[CH2:3][CH2:2]1.[CH3:7][CH:8]([O:11][C:12]1[CH:21]=[CH:20][C:15]([O:16][CH2:17][CH2:18][NH2:19])=[CH:14][CH:13]=1)[CH2:9][CH3:10].C(N(CC)CC)C.Cl>C(Cl)Cl>[CH3:7][CH:8]([O:11][C:12]1[CH:21]=[CH:20][C:15]([O:16][CH2:17][CH2:18][NH:19][C:4]([CH:1]2[CH2:3][CH2:2]2)=[O:5])=[CH:14][CH:13]=1)[CH2:9][CH3:10]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 77637Cyclopropanecarbonyl chlorideHCID 142781892-{4-[(Butan-2-yl)oxy]phenoxy}ethan-1-amine

Product 1

HCID 14278190N-{2-[4-(1-methylprop-1-yloxy)-phenoxy]-ethyl}-cyclopropanecarboxamideYield 74.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

At 5° C., 3.4 g of cyclopropanecarboxylic chloride was dripped into a solution of 6.5 g of 2-[4-(1-methylprop-1-yloxy)-phenoxy]-ethylamine and 3.5 g of triethylamine in 100 ml of absolute methylene chloride. After the mixture had been stirred for 8 hours it was poured onto 200 g of ice/water and the resultant solution was adjusted to a pH of 2 with 2N aqueous hydrochloric acid. The aqueous phase was then extracted twice, each time with 50 ml of methylene chloride, and the combined organic phases were washed with saturated sodium carbonate solution and water, and dried over sodium sulfate. After removal of the solvent under reduced pressure and recrystallization from cyclohexane, there was obtained 6.4 g of N-{2-[4-(1-methylprop-1-yloxy)-phenoxy]-ethyl}-cyclopropanecarboxamide (compound no. 2); m.p.: 65°-68° C.

Workup

  1. customAt 5° C.
  2. extractionThe aqueous phase was then extracted twice
  3. washeach time with 50 ml of methylene chloride, and the combined organic phases were washed with saturated sodium carbonate solution and water
  4. dry with materialdried over sodium sulfate
  5. customAfter removal of the solvent
  6. customunder reduced pressure and recrystallization from cyclohexane

Sources & evidence

ORD record
ord-534d9857ed8646fabf1bac97476c1a87
Source dataset
uspto-grants-1990_10
Patent number
US04960796

Reaction notes

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