Triethylamine → 2-Morpholinoethyl N-[(5S)-3,9,10,11-tetramethoxy-6,7-dihydro-5H-dibenzo[a,c]cyclohepten-5-yl]carbamate

HRID 2085027Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:12]3[C:13]([O:21][CH3:22])=[C:14]([O:19][CH3:20])[C:15]([O:17][CH3:18])=[CH:16][C:11]=3[CH2:10][CH2:9][C@H:8]([NH2:23])[C:7]=2[CH:24]=1.C1C([N+]([O-])=O)=CC=C([Cl-][C:35]([O-:37])=[O:36])C=1.C(N(CC)CC)C.O[CH2:46][CH2:47][N:48]1[CH2:53][CH2:52][O:51][CH2:50][CH2:49]1>C(#N)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:12]3[C:13]([O:21][CH3:22])=[C:14]([O:19][CH3:20])[C:15]([O:17][CH3:18])=[CH:16][C:11]=3[CH2:10][CH2:9][C@H:8]([NH:23][C:35](=[O:36])[O:37][CH2:46][CH2:47][N:48]3[CH2:53][CH2:52][O:51][CH2:50][CH2:49]3)[C:7]=2[CH:24]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A solution of (5S)-3,9,10,11-tetramethoxy-6,7-dihydro-5H-dibenzo[a,c]cyclohepten-5-ylamine [Collect. Czech. Chem. Commun. 1999, 64(2), 217-228] (0.263 g; 0.8 mmol), 4-nitrophenylchloroformate (0.177 g; 0.88 mmol) and triethylamine (0.123 ml; 0.88 mmol) in acetonitrile (5 ml) was stirred under argon atmosphere for 2 hours at ambient temperature; 4-(2-hydroxyethyl)morpholine (0.145 ml; 1.2 mmol) in solution in acetonitrile (2 ml) was then added to the above solution. The mixture was heated at 60° C. overnight. After evaporation to dryness, the residue was purified by flash chromatography, eluted with ethanol/dichloromethane (4/96) to give the title compound.

Workup

customAfter evaporation to dryness
customthe residue was purified by flash chromatography
washeluted with ethanol/dichloromethane (4/96)

Sources & evidence

ORD record: ord-f255478d53984655ba06491d719d4864
Source dataset: uspto-grants-2004_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06720323B2

Reaction notes

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