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

HRID 26423
Notes
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Reaction equation

HRID 26423 reaction equation
[CH3:1][N:2]1[CH2:8][CH2:7][CH2:6][C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([O:15][CH3:16])[CH:10]=2)=[C:4]([CH2:17][C:18]([CH3:20])=O)[C:3]1=[O:21].[NH:22]1[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1.Cl.C([BH3-])#N.[Na+]>CO>[CH3:1][N:2]1[CH2:8][CH2:7][CH2:6][C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([O:15][CH3:16])[CH:10]=2)=[C:4]([CH2:17][CH:18]([N:22]2[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]2)[CH3:20])[C:3]1=[O:21]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 8082PiperidineHCID 5003444Sodium cyanoborohydride2×HCID 20332941HCID 20332941, compound

Product 1

HCID 203329351-methyl-3-(2-piperidinopropyl)-4-(3-methoxyphenyl)-1,5,6,7-tetrahydro-2H-azepinone

Reagents, catalysts & solvents 1

HCID 887
Methanol
Solvent

Procedure

The solution of 8.0 g of 1-methyl-3-acetonyl-4-(3-methoxyphenyl)-1,5,6,7-tetrahydro-2H-azepinone, 14.2 g of piperidine, 6.4 ml of 5 N methanolic hydrogen chloride and 1.91 g of sodium cyanoborohydride in 100 ml of methanol is refluxed overnight. An additional portion of 1.91 g of sodium cyanoborohydride is added and refluxing continued for another day. The solution is cooled, acidified with a 35 ml of concentrated hydrochloric acid and evaporated. The residue is diluted with 100 ml of water, the aqueous solution washed with benzene, filtered, basified with 65 ml 3 N aqueous sodium hydroxide and extracted with diethyl ether. The extract is dried, evaporated and the residue crystallized from petroleum ether and recrystallized from hexane, to yield the 1-methyl-3-(2-piperidinopropyl)-4-(3-methoxyphenyl)-1,5,6,7-tetrahydro-2H-azepinone melting at 101°-103°.

Workup

  1. temperaturerefluxing
  2. waitcontinued for another day
  3. temperatureThe solution is cooled
  4. customevaporated
  5. additionThe residue is diluted with 100 ml of water
  6. washthe aqueous solution washed with benzene
  7. filtrationfiltered
  8. extractionextracted with diethyl ether
  9. customThe extract is dried
  10. customevaporated
  11. customthe residue crystallized from petroleum ether
  12. customrecrystallized from hexane

Sources & evidence

ORD record
ord-08c41572ed104954a8ff0cf777e65a21
Source dataset
uspto-grants-1979_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04150129

Reaction notes

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