Potassium Carbonate → (1-benzyl-5-chloro-2,3,6,7-tetrahydro-1H-azepin-4-yl)-phenyl-methanone

HRID 400436Notes

Reaction equation

HRID 400436 reaction equation
[CH2:1]([N:8]1[CH2:14][CH2:13][C:12]([Cl:15])=[C:11]([CH:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[OH:17])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+]>ClCCl>[CH2:1]([N:8]1[CH2:14][CH2:13][C:12]([Cl:15])=[C:11]([C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:17])[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 86686039(1-benzyl-5-chloro-2,3,6,7-tetrahydro-1H-azepin-4-yl)-phenyl-methanolHCID 178418287HCID 178418287, compound

Product 1

HCID 69190815(1-benzyl-5-chloro-2,3,6,7-tetrahydro-1H-azepin-4-yl)-phenyl-methanoneYield 73%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

89 g (1-benzyl-5-chloro-2,3,6,7-tetrahydro-1H-azepin-4-yl)-phenyl-methanol in 800 mL dichlormethane was dropped to 115.4 g pyridiniumchlorchromate in 600 mL dichlormethane. The reaction was stirred 2.5 days at RT. Potassiumcarbonate-solution was added to the reaction. The mixture was stirred 2 h at RT and filtered over celite. The layers were separated and the organic layer was washed with water. The solvent was removed and the residue was purified by chromatography on silica gel (toluol/EE: 8.5:1.5). The solvent was removed and 64.6 g of the desired compound was obtained. Rf: 0.5 (toluol/EE: 8.5:1.5)

Workup

  1. stirringThe mixture was stirred 2 h at RT
  2. filtrationfiltered over celite
  3. customThe layers were separated
  4. washthe organic layer was washed with water
  5. customThe solvent was removed
  6. customthe residue was purified by chromatography on silica gel (toluol/EE: 8.5:1.5)
  7. customThe solvent was removed

Sources & evidence

ORD record
ord-94a323917fa044978eb467dc0e4d9a58
Source dataset
uspto-grants-2014_06
Patent number
US08741892B2

Reaction notes

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