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

HRID 239113Notes

Reaction equation

HRID 239113 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. Potassium carbonate 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 to yield 64.6 g of the desired compound. 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

Sources & evidence

ORD record
ord-6a15ce433d6f4bb6a723541e70a31b3b
Source dataset
uspto-grants-2014_02
Patent number
US08642774B2

Reaction notes

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