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

HRID 1648929Notes

Reaction equation

HRID 1648929 reaction equation
Cl[C:2]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:3].C([N:19]1[CH2:25][CH2:24][C:23]([C:26]#[N:27])=[C:22]([Cl:28])[CH2:21][CH2:20]1)C1C=CC=CC=1>C(Cl)Cl>[Cl:28][C:22]1[CH2:21][CH2:20][N:19]([C:2]([O:4][CH2:5][C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)=[O:3])[CH2:25][CH2:24][C:23]=1[C:26]#[N:27]

Participants

4

Reactant 2

HCID 10387Benzyl chloroformateHCID 130720321-Benzyl-4-chloro-5-cyano-2,3,6,7-tetrahydro-1H-azepine

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

4.3 gm=3.9 ml (0.025 mol) of benzyl chloroformate dissolved in 15 ml of methylene chloride, were added dropwise to a solution of 4.9 gm (0.02 mol) of 1-benzyl-4-chloro-5-cyano-2,3,6,7-tetrahydro-1H-azepine in 500 ml of methylene chloride while stirring at room temperature, whereby the temperature rose by 5° C. The mixture was stirred for 5 hours at room temperature and then allowed to stand overnight. The solvent was then removed in a rotary evaporator, and the residue was purified on a silicagel column (toluene/ethyl acetate=8:2). After the corresponding fractions had been concentrated by evaporation, a slightly yellowish oil was obtained with solidified upon standing.

Workup

  1. customrose by 5° C
  2. stirringThe mixture was stirred for 5 hours at room temperature
  3. customThe solvent was then removed in a rotary evaporator
  4. customthe residue was purified on a silicagel column (toluene/ethyl acetate=8:2)
  5. concentrationAfter the corresponding fractions had been concentrated by evaporation
  6. customa slightly yellowish oil was obtained with solidified

Sources & evidence

ORD record
ord-9ee8245e49ec4a498c0416aea38e1629
Source dataset
uspto-grants-1983_11
Patent number
US04414225

Reaction notes

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