Dimethylformamide → HCID 21330554, compound

HRID 1391251Notes

Reaction equation

HRID 1391251 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]23[CH2:18][CH2:17][CH2:16][CH:10]2[CH2:11][NH:12][CH2:13][CH2:14][CH2:15]3)[CH:6]=[CH:7][CH:8]=1.[CH:19]1([C:22](Cl)=[O:23])[CH2:21][CH2:20]1.CN(C)C=O>C(N(CC)CC)C>[CH:19]1([C:22]([N:12]2[CH2:13][CH2:14][CH2:15][C:9]3([C:5]4[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=4)[CH2:18][CH2:17][CH2:16][CH:10]3[CH2:11]2)=[O:23])[CH2:21][CH2:20]1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 77637Cyclopropanecarbonyl chlorideHCID 21330522HCID 21330522, compound

Product 1

HCID 21330554HCID 21330554, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

A solution of 1.1 g. of 5a-(3-methoxyphenyl)-decahydrocyclopent[c]azepine and 1.3 g. of cyclopropylformyl chloride in 20 ml. of N,N-dimethylformamide containing 1.4 g. of triethylamine was stirred at 25° C. for eight hours. The reaction mixture then was added to 200 ml. of water, and the aqueous solution was extracted several times with diethyl ether. The ethereal extracts were combined, and the solvent was removed therefrom by evaporation under reduced pressure to provide 2-cyclopropylformyl-5a-(3-methoxyphenyl)-decahydrocyclopent[c]azepine. The product so formed was dissolved in 70 ml. of tetrahydrofuran containing 1 g. of lithium aluminum hydride, and the reaction mixture was heated at reflux and stirred for three hours. The reaction mixture was then cooled to 25° C. and diluted by the dropwise addition of 30 ml. of ethyl acetate. The tetrahydrofuran solution was decanted, diluted with diethyl ether, washed with water, and dried. Removal of the solvent by evaporation under reduced pressure provided 2-cyclopropylmethyl-5a-(3-methoxyphenyl)-decahydrocyclopent[c]azepine as an oil. The oil so formed was dissolved in 50 ml. of diethyl ether through which was bubbled hydrogen chloride gas, thus forming the hydrochloride salt of the above-named compound, which precipitated out of solution. The precipitate was collected by filtration and recrystallized from 25 ml. of diisopropyl ether and 100 ml. of ethyl acetate to afford 0.75 g. of ethyl acetate to afford 0.75 g. of 2-cyclopropylmethyl-5a-(3-methoxyphenyl)-decahydrocyclopent[c]azepine hydrochloride. M.P. 154°-156° C.

Workup

  1. additionThe reaction mixture then was added to 200 ml
  2. extractionof water, and the aqueous solution was extracted several times with diethyl ether
  3. customthe solvent was removed
  4. customby evaporation under reduced pressure

Sources & evidence

ORD record
ord-6d223685c43e42e2b3ea49d62050f460
Source dataset
uspto-grants-1979_02
Patent number
US04141893

Reaction notes

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