Cyclopropanecarbonyl chloride → HCID 13324059, compound

HRID 1156545Notes

Reaction equation

HRID 1156545 reaction equation
[CH:1]1([C:4](Cl)=O)[CH2:3][CH2:2]1.[K].[CH3:8][O:9][C:10]1[CH:11]=[C:12]([C:16]2([CH2:22][CH2:23][NH2:24])[CH2:21][CH2:20][CH2:19][CH:18]=[CH:17]2)[CH:13]=[CH:14][CH:15]=1>C(Cl)Cl.CCOCC>[CH:1]1([CH2:4][NH:24][CH2:23][CH2:22][C:16]2([C:12]3[CH:13]=[CH:14][CH:15]=[C:10]([O:9][CH3:8])[CH:11]=3)[CH2:21][CH2:20][CH2:19][CH:18]=[CH:17]2)[CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 77637Cyclopropanecarbonyl chlorideHCID 5462222PotassiumHCID 12838394HCID 12838394, compound

Product 1

HCID 13324059HCID 13324059, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Procedure

3.45 g of cyclopropanecarboxylic acid chloride are placed in 50 ml of methylene chloride, whereafter 5.0 g of potassium carbnate are added, and then a solution of 7.0 g of 1-(m-methoxyphenyl)-2-cyclohexene-1-ethylamine in 10 ml of methylene chloride is added dropwise while stirring. The mixture is stirred at room temperature overnight and subsequently at reflux for 30 minutes and cooled. Then, the precipitate is removed by filtration under suction, the filtrate is evaporated, and the oil obtained is taken up in ether. The ethereal solution is washed with 1 N hydrochloric acid and subsequently with water, dried over magnesium sulfate and evaporated, and N-[2-[1-(m-methoxyphenyl)-2-cyclohexen-1-yl]ethyl]-cyclopropanecarboxamide remains as the residue. 6.5 g of this compound, dissolved in 30 ml of absolute tetrahydrofuran, are added dropwise to a dispersion of 6 g of lithium aluminum hydride in 100 ml of absolute tetrahydrofuran. The mixture is boiled at reflux for 3 hours, cooled and worked-up in the usual manner, and there is obtained N-(cyclopropylmethyl)-1-(m-methoxyphenyl)-2-cyclohexene-1-ethylamine, the hydrochloride of which melts at 141°-142° C.

Workup

  1. additionare added
  2. stirringThe mixture is stirred at room temperature overnight
  3. temperaturesubsequently at reflux for 30 minutes
  4. temperaturecooled
  5. customThen, the precipitate is removed by filtration under suction
  6. customthe filtrate is evaporated
  7. customthe oil obtained
  8. washThe ethereal solution is washed with 1 N hydrochloric acid and subsequently with water
  9. dry with materialdried over magnesium sulfate
  10. customevaporated
  11. dissolution6.5 g of this compound, dissolved in 30 ml of absolute tetrahydrofuran
  12. additionare added dropwise to a dispersion of 6 g of lithium aluminum hydride in 100 ml of absolute tetrahydrofuran
  13. temperatureat reflux for 3 hours
  14. temperaturecooled

Sources & evidence

ORD record
ord-1e505189456c42ca875ec5e1ffa69db4
Source dataset
uspto-grants-1982_06
Patent number
US04336268

Reaction notes

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