Hydrochloric Acid → 3-(2-piperidinopropyl)-4-(3-methoxyphenyl)-1,5,6,7-tetrahydro-2H-azepinone

HRID 26419Notes

Reaction equation

HRID 26419 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[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1.Cl.C([BH3-])#N.[Na+]>CO>[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)[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1

Participants

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 8082PiperidineHCID 5003444Sodium cyanoborohydride2×HCID 203329343-acetonyl-4-(3-methoxyphenyl)-1,5,6,7-tetrahydro-2H-azepinone

Product 1

HCID 203329443-(2-piperidinopropyl)-4-(3-methoxyphenyl)-1,5,6,7-tetrahydro-2H-azepinone

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The solution of 8.0 g of 3-acetonyl-4-(3-methoxyphenyl)-1,5,6,7-tetrahydro-2H-azepinone, 14.95 g of piperidine, 6.6 ml of 5 N methanolic hydrogen chloride and 1.9 g of sodium cyanoborohydride in 120 ml of methanol is refluxed overnight. An additional portion of 0.95 g of sodium cyanoborohydride is added and refluxing continued for 24 hours. The mixture is cooled to 0°, 30 ml of concentrated hydrochloric acid are added and the solution concentrated. The concentrate is diluted with 100 ml of water, the solution washed with benzene and rendered basic with 70 ml of 3 N aqueous sodium hydroxide. It is extracted with diethyl ether, the extract evaporated and the residue crystallized from petroleum ether and hexane, to yield the 3-(2-piperidinopropyl)-4-(3-methoxyphenyl)-1,5,6,7-tetrahydro-2H-azepinone of the formula ##STR7## melting at 97° to 99°.

Workup

  1. temperaturerefluxing
  2. temperatureThe mixture is cooled to 0°
  3. concentrationthe solution concentrated
  4. additionThe concentrate is diluted with 100 ml of water
  5. washthe solution washed with benzene
  6. extractionIt is extracted with diethyl ether
  7. customthe extract evaporated
  8. customthe residue crystallized from petroleum ether and hexane

Sources & evidence

ORD record
ord-481dd5b797924028a82d5f5e0d0d8591
Source dataset
uspto-grants-1979_04
Patent number
US04150129

Reaction notes

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