Water → 3-(2-pyrrolidinopropyl)-4-(3-methoxyphenyl)-1,5,6,7-tetrahydro-2H-azepinone

HRID 26421Notes

Reaction equation

HRID 26421 reaction equation
[CH2:1]([C:5]1[C:6](=[O:20])[NH:7][CH2:8][CH2:9][CH2:10][C:11]=1[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[CH:13]=1)[C:2]([CH3:4])=O.[NH:21]1[CH2:25][CH2:24][CH2:23][CH2:22]1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1C=CC=CC=1>[N:21]1([CH:2]([CH3:4])[CH2:1][C:5]2[C:6](=[O:20])[NH:7][CH2:8][CH2:9][CH2:10][C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[CH:13]=2)[CH2:25][CH2:24][CH2:23][CH2:22]1

Participants

6

Reactant 4

HCID 962WaterHCID 31268PyrrolidineHCID 521998p-Toluenesulfonic acid monohydrateHCID 203329343-acetonyl-4-(3-methoxyphenyl)-1,5,6,7-tetrahydro-2H-azepinone

Product 1

HCID 203329363-(2-pyrrolidinopropyl)-4-(3-methoxyphenyl)-1,5,6,7-tetrahydro-2H-azepinone

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

The solution of 1.36 g of 3-acetonyl-4-(3-methoxyphenyl)-1,5,6,7-tetrahydro-2H-azepinone, 0.52 g of pyrrolidine and 0.1 g of p-toluenesulfonic acid hydrate in 10 ml of benzene is refluxed with water separation for 4 hours and evaporated. The residue is dissolved in 15 ml of ethanol and the solution hydrogenated over 0.1 g of platinum oxide at atmospheric pressure and room temperature. The mixture is filtered, the filtrate evaporated and the resulting oil dissolved in 2 N hydrochloric acid. The solution is washed with benzene, basified with 3 N aqueous sodium hydroxide and extracted with diethyl ether. The extract is dried, evaporated and the residue recrystallized from petroleum ether and hexane, to yield the 3-(2-pyrrolidinopropyl)-4-(3-methoxyphenyl)-1,5,6,7-tetrahydro-2H-azepinone melting at 94° to 96°.

Workup

  1. customevaporated
  2. dissolutionThe residue is dissolved in 15 ml of ethanol
  3. customhydrogenated over 0.1 g of platinum oxide at atmospheric pressure and room temperature
  4. filtrationThe mixture is filtered
  5. customthe filtrate evaporated
  6. dissolutionthe resulting oil dissolved in 2 N hydrochloric acid
  7. washThe solution is washed with benzene
  8. extractionextracted with diethyl ether
  9. customThe extract is dried
  10. customevaporated
  11. customthe residue recrystallized from petroleum ether and hexane

Sources & evidence

ORD record
ord-760a98293ac541fb91f5ad4cec365ad5
Source dataset
uspto-grants-1979_04
Patent number
US04150129

Reaction notes

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