HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

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

HRID 1706910
Notes
Print preview

Reaction equation

HRID 1706910 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 241
Benzene
Solvent

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-79e1020a9f72431993745dc4f64bd94d
Source dataset
uspto-grants-1980_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04209514

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes