Dimethylformamide → 3-(4-[2-([10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-yl]-methyl-amino)-ethoxy]-phenyl)-2-ethoxypropanoic acid ethyl ester

HRID 2086032Notes

Reaction equation

Cl.[CH3:2][NH:3][CH:4]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[CH2:8][CH2:7][C:6]2[CH:15]=[CH:16][CH:17]=[CH:18][C:5]1=2.[CH2:19]([O:21][C:22](=[O:38])[CH:23]([O:35][CH2:36][CH3:37])[CH2:24][C:25]1[CH:30]=[CH:29][C:28]([O:31][CH2:32][CH2:33]Br)=[CH:27][CH:26]=1)[CH3:20].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O.C1C=CC=CC=1>[CH2:19]([O:21][C:22](=[O:38])[CH:23]([O:35][CH2:36][CH3:37])[CH2:24][C:25]1[CH:30]=[CH:29][C:28]([O:31][CH2:32][CH2:33][N:3]([CH:4]2[C:5]3[CH:18]=[CH:17][CH:16]=[CH:15][C:6]=3[CH2:7][CH2:8][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]2=3)[CH3:2])=[CH:27][CH:26]=1)[CH3:20]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 5-(methylamino)-10,11-dihydro-5H-dibenzo[a,d]cycloheptene hydrochloride (1.8 g, 6.94 mmol), ethyl-3-(4-bromethoxyphenyl)-2-ethoxypropanoate (2.4 g, 6.95 mmol), potassium carbonate (2.9 g, 21 mmol) and dimethylformamide (7 ml) was heated at 100° C. for 5 h. Benzene (200 ml) and water (200 ml) were added and the phases were separated. The organic phase was dried and the solvent evaporated in vacuo. The residue was purified by chromatography on silica gel eluting with benzene/chloroform to give 2.2 g (65%) of the title compound as an oil. RF=0.60 (chloroform/ethanol/ammonia=20:2:0.1)

Workup

customthe phases were separated
customThe organic phase was dried
customthe solvent evaporated in vacuo
customThe residue was purified by chromatography on silica gel eluting with benzene/chloroform

Sources & evidence

ORD record: ord-70e62693081640a0bd7677859949f12a
Source dataset: uspto-grants-2004_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06723731B2

Reaction notes

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