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

HRID 323597
Notes
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Reaction equation

HRID 323597 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.Br[CH2:20][CH2:21][O:22][C:23]1[CH:28]=[CH:27][C:26]([CH2:29][CH:30]([O:36][CH2:37][CH3:38])[C:31]([O:33][CH2:34][CH3:35])=[O:32])=[CH:25][CH:24]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O.C1C=CC=CC=1>[CH2:34]([O:33][C:31](=[O:32])[CH:30]([O:36][CH2:37][CH3:38])[CH2:29][C:26]1[CH:27]=[CH:28][C:23]([O:22][CH2:21][CH2:20][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:24][CH:25]=1)[CH3:35]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 11002461Ethyl 2-ethoxy-3-[4-(2-bromoethoxy)-phenyl]propanoateHCID 227277975-(Methylamino)-10,11-dihydro-5h-dibenzo[a,d]cycloheptene hydrochloride

Product 1

HCID 98700773-(4-[2-([10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-yl]-methyl-amino)-ethoxy]-phenyl)-2-ethoxypropanoic acid ethyl ester
Yield 65%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 962WaterSolvent

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

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

Sources & evidence

ORD record
ord-4ab34211c26b4172b4b07729bae6f28e
Source dataset
uspto-grants-2001_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06214820B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes