Benzyl 4-chloro-5-cyano-2,3,6,7-tetrahydro-1H-azepine-1-carboxylate → 4-Chloro-5-cyano-2,3,6,7-tetrahydro-1H-azepine hydrochloride

HRID 1648930Notes

Reaction equation

HRID 1648930 reaction equation
[Cl:1][C:2]1[CH2:3][CH2:4][N:5](C(OCC2C=CC=CC=2)=O)[CH2:6][CH2:7][C:8]=1[C:9]#[N:10].[H][H]>C(O)C.Cl.[Pd]>[ClH:1].[Cl:1][C:2]1[CH2:3][CH2:4][NH:5][CH2:6][CH2:7][C:8]=1[C:9]#[N:10]

Participants

6

Reactant 2

HCID 13072036Benzyl 4-chloro-5-cyano-2,3,6,7-tetrahydro-1H-azepine-1-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 204813254-Chloro-5-cyano-2,3,6,7-tetrahydro-1H-azepine hydrochloride

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

1.45 gm (0.005 mol) of benzyl 4-chloro-5-cyano-2,3,6,7-tetrahydro-1H-1-azepine-carboxylate were dissolved in 20 ml of ethyl alcohol by addition of 0.9 ml of semiconcentrated hydrochloric acid, and after the addition of 0.2 gm of palladium-on-charcoal, the mixture was hydrogenated in an autoclave at room temperature and under a hydrogen pressure of 5 bars. After half an hour, the uptake of hydrogen had ended. The catalyst was filtered off, and the filtrate was evaporated in vacuo. The residue was recrystallized from isopropyl alcohol.

Workup

  1. customwas hydrogenated in an autoclave at room temperature and under a hydrogen
  2. waitAfter half an hour
  3. filtrationThe catalyst was filtered off
  4. customthe filtrate was evaporated in vacuo
  5. customThe residue was recrystallized from isopropyl alcohol

Sources & evidence

ORD record
ord-a6fa2d10549c4504a613980442eb2a64
Source dataset
uspto-grants-1983_11
Patent number
US04414225

Reaction notes

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