Potassium Iodide → 1-(3-(10,11-dihydro-5H-dibenz[b,f]azepin-5-yl)-1-propyl)4-piperidineacetic acid ethyl ester

HRID 1166420Notes

Reaction equation

Cl[CH2:2][CH2:3][CH2:4][N:5]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[CH2:9][CH2:8][C:7]2[CH:16]=[CH:17][CH:18]=[CH:19][C:6]1=2.[I-].[K+].C(=O)([O-])[O-].[K+].[K+].[CH2:28]([O:30][C:31](=[O:39])[CH2:32][CH:33]1[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]1)[CH3:29]>C(C(C)=O)C>[CH2:28]([O:30][C:31](=[O:39])[CH2:32][CH:33]1[CH2:38][CH2:37][N:36]([CH2:2][CH2:3][CH2:4][N:5]2[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[CH2:9][CH2:8][C:7]3[CH:16]=[CH:17][CH:18]=[CH:19][C:6]2=3)[CH2:35][CH2:34]1)[CH3:29]

Participants

Conditions

Temperature: 75 °C

Procedure

A mixture of 5-(3-chloropropyl)-10,11-dihydro-5H-dibenz[b,f]azepine (1.5 g, 0.0055 mol, prepared similarly as described in example 1) and potassium iodide (5.4 g, 0.0327 mol) in methyl ethyl ketone (100 ml) was heated at reflux temperature for 2.5 h. Potassium carbonate (1.5 g, 0.0109 mol) and 4-piperidineacetic acid ethyl ester (1.4 g, 0.0082 mmol, described in J. Am. Chem. Soc., Vol. 75, 6249, 1953) were added and the reaction mixture was stirred at 75° C. overnight. After cooling, the reaction mixture was filtered (Hyflo) and the solvent was evaporated in vacuo. The residue was purified by flash chromatography on silica gel (150 g) using a gradient of heptane and ethyl acetate (1:1→3:7), to give 0.6 g of 1-(3-(10,11-dihydro-5H-dibenz[b,f]azepin-5-yl)-1-propyl)-4-piperidineacetic acid ethyl ester as an oil.

Workup

customprepared similarly
temperaturewas heated
temperatureat reflux temperature for 2.5 h
temperatureAfter cooling
filtrationthe reaction mixture was filtered (Hyflo)
customthe solvent was evaporated in vacuo
customThe residue was purified by flash chromatography on silica gel (150 g)

Sources & evidence

ORD record: ord-cac3134619164b71bacedc19bb380efc
Source dataset: uspto-grants-2003_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06613791B1

Reaction notes

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