Potassium Carbonate → HCID 59597380, compound

HRID 218648Notes

Reaction equation

[CH3:1][N:2]([CH3:33])[C:3]1[CH:8]=[CH:7][C:6]([CH2:9][N:10]([C:24]2[CH:29]=[CH:28][C:27]([CH:30]([CH3:32])[CH3:31])=[CH:26][CH:25]=2)[C:11]([CH:13]2[C:22]3[C:17](=[CH:18][C:19]([OH:23])=[CH:20][CH:21]=3)[CH2:16][CH2:15][CH2:14]2)=[O:12])=[CH:5][CH:4]=1.Cl.Cl[CH2:36][CH2:37][N:38]([CH3:40])[CH3:39].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:39][N:38]([CH3:40])[CH2:37][CH2:36][O:23][C:19]1[CH:18]=[C:17]2[C:22](=[CH:21][CH:20]=1)[CH:13]([C:11]([N:10]([CH2:9][C:6]1[CH:7]=[CH:8][C:3]([N:2]([CH3:33])[CH3:1])=[CH:4][CH:5]=1)[C:24]1[CH:25]=[CH:26][C:27]([CH:30]([CH3:31])[CH3:32])=[CH:28][CH:29]=1)=[O:12])[CH2:14][CH2:15][CH2:16]2

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of N-[(4-dimethylaminophenyl)methyl]-6-hydroxy-N-(4-isopropylphenyl)-1,2,3,4-tetrahydronaphthalene-1-carboxamide (0.66 g) in dimethylformamide (10 mL) were added 2-chloro-N,N-dimethylethylamine hydrochloride (0.26 g) and potassium carbonate (0.62 g), and the mixture was stirred with heating at 50° C. for 3 hr. The reaction mixture was partitioned between water and ethyl acetate. The organic layer was washed with saturated brine and dried over magnesium sulfate. The solvent was evaporated, and the residue was purified by silica gel column chromatography to give 6-[2-(dimethylamino)ethoxy]-N-[(4-dimethylaminophenyl)methyl]-N-(4-isopropylphenyl)-1,2,3,4-tetrahydronaphthalene-1-carboxamide ⅕ hydrate (0.1 g). melting point: 132.6° C.

Workup

customThe reaction mixture was partitioned between water and ethyl acetate
washThe organic layer was washed with saturated brine
dry with materialdried over magnesium sulfate
customThe solvent was evaporated
customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-799eca7bb5c0487db4225e7753300199
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08198454B2

Reaction notes

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