Hydrogen Bromide → 4-Chloro-5-formyl-2,3,6,7-tetrahydro-1H-azepine hydrobromide

HRID 1648928Notes

Reaction equation

HRID 1648928 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[CH:9]=[O:10].[BrH:21]>C(O)(=O)C>[BrH:21].[Cl:1][C:2]1[CH2:3][CH2:4][NH:5][CH2:6][CH2:7][C:8]=1[CH:9]=[O:10]

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 20481342Benzyl-4-chloro-5-formyl-2,3,6,7-tetrahydro-1H-1-azepinecarboxylate

Product 1

HCID 204813404-Chloro-5-formyl-2,3,6,7-tetrahydro-1H-azepine hydrobromide

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

10.5 gm (0.036 mol) of benzyl 4-chloro-5-formyl-2,3,6,7-tetrahydro-1H-1-azepine-carboxylate were mixed with 100 ml of a 40% solution of hydrogen bromide in glacial acetic acid, while stirring and cooling with ice. The mixture was then stirred for 3 hours at room temperature. It was then concentrated by evaporation in a rotary evaporator, and the residue was triturated with ether. After the ether had been decanted several times, the product was suction-filtered and washed twice with absolute ether.

Workup

  1. temperaturecooling with ice
  2. stirringThe mixture was then stirred for 3 hours at room temperature
  3. concentrationIt was then concentrated by evaporation in a rotary evaporator
  4. customthe residue was triturated with ether
  5. customAfter the ether had been decanted several times
  6. filtrationthe product was suction-filtered
  7. washwashed twice with absolute ether

Sources & evidence

ORD record
ord-9eea466973144fb0a0aa34dc55483a3b
Source dataset
uspto-grants-1983_11
Patent number
US04414225

Reaction notes

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