Potassium Iodide → HCID 54010195, compound

HRID 1979035Notes

Reaction equation

HRID 1979035 reaction equation
Cl.[CH2:2]([O:4][C:5]([CH:7]1[CH2:12][CH2:11][CH2:10][CH2:9][NH:8]1)=[O:6])[CH3:3].Cl[CH2:14][CH2:15][CH2:16][N:17]1[C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=2[CH2:21][CH2:20][C:19]2[CH:28]=[CH:29][CH:30]=[CH:31][C:18]1=2.[I-].[K+].C(=O)([O-])[O-].[K+].[K+]>O.CN(C)C=O.C(#N)C>[CH2:2]([O:4][C:5]([CH:7]1[CH2:12][CH2:11][CH2:10][CH2:9][N:8]1[CH2:14][CH2:15][CH2:16][N:17]1[C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=2[CH2:21][CH2:20][C:19]2[CH:28]=[CH:29][CH:30]=[CH:31][C:18]1=2)=[O:6])[CH3:3]

Participants

8

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 2867795-(3-Chloropropyl)-10,11-dihydro-5H-dibenz[b,f]azepineHCID 12436225Ethyl piperidine-2-carboxylate--hydrogen chloride (1/1)

Product 1

HCID 54010195HCID 54010195, compoundYield 97%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Procedure

A mixture of 2-piperidinecarboxylic acid ethyl ester hydrochloride (0.60 g, 0.003 mol), acetonitrile (10 ml), 5-(3-chloropropyl)-10,11-dihydro-5H-dibenzo[b,f]azepine (0.60 g, 0.002 mol, prepared similarly as described in example 1), potassium iodide (0.40 g, 0.002 mol), potassium carbonate (1.03 g, 0.008 mol) and N,N-dimethylformamide (5 ml) was heated at reflux temperature for 85 h. Water (50 ml) was added, and the aqueous solution was extracted with ethyl acetate (3×20 ml). The combined organic extracts were washed with brine (2×50 ml), dried (MgSO4) and concentrated in vacuo. The product was purified by column chromatography on silica gel (15 g) using a gradient of heptane and ethyl acetate (100:0→100:25), affording 0.83 g (97%) of 1-(3-(10,11-dihydro-5H-dibenz[b,f]azepin-5-yl)-1-propyl)-2-piperidinecarboxylic acid ethyl ester as an oil.

Workup

  1. customprepared similarly
  2. temperaturewas heated
  3. temperatureat reflux temperature for 85 h
  4. extractionthe aqueous solution was extracted with ethyl acetate (3×20 ml)
  5. washThe combined organic extracts were washed with brine (2×50 ml)
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo
  8. customThe product was purified by column chromatography on silica gel (15 g)

Sources & evidence

ORD record
ord-c4a938750eca47cca6b70fbdd8f07bc3
Source dataset
uspto-grants-2001_05
Patent number
US06239148B1

Reaction notes

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