Pyridine → HCID 58494891, compound

HRID 516225Notes

Reaction equation

HRID 516225 reaction equation
[CH2:1]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[CH2:5][CH2:4][NH:3][CH2:2]1.N1C=CC=CC=1.Cl[C:19]([O:21][CH2:22][CH3:23])=[O:20]>ClCCl>[CH2:5]1[C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[CH2:1][CH2:2][N:3]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH2:4]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 10928Ethyl chloroformateHCID 14002432,3,4,5-Tetrahydro-1H-benzo(d)azepine

Product 1

HCID 58494891HCID 58494891, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 1.75 g of 2,3,4,5-tetrahydro-1H-3-benzazepine in 20 ml of dichloromethane was added 2.884 ml of pyridine. The reaction mixture was ice-cooled, and 1.705 ml of ethyl chloroformate which had been dissolved in 5 ml of dichloromethane was added dropwise thereto, followed by stirring overnight. The reaction mixture was concentrated under reduced pressure and the residue was purified by silica gel chromatography (elution solvent: HEX-EtOAc) to obtain 2.15 g of ethyl 1,2,4,5-tetrahydro-3H-3-benzazepine-3-carboxylate as a pale yellow oily substance.

Workup

  1. temperaturecooled
  2. additionwas added dropwise
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. customthe residue was purified by silica gel chromatography (elution solvent: HEX-EtOAc)

Sources & evidence

ORD record
ord-93406dd2c9d941eea68a38c7d3f3e78d
Source dataset
uspto-grants-2015_08
Patent number
US09108977B2

Reaction notes

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