Potassium Carbonate → HCID 67248303, compound

HRID 2175083Notes

Reaction equation

[CH3:1][C:2]1([CH3:26])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6]([C:14]3[N:19]=[C:18]([N:20]4[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]4)[CH:17]=[CH:16][CH:15]=3)[CH:5]=[CH:4][C:3]1=2.C(=O)([O-])[O-].[K+].[K+].[C:33]([O:36][CH2:37][CH2:38][CH2:39][CH2:40]Br)(=[O:35])[CH3:34]>CN(C=O)C>[CH3:1][C:2]1([CH3:26])[CH2:11][CH2:10][C:9]([CH3:12])([CH3:13])[C:8]2[CH:7]=[C:6]([C:14]3[N:19]=[C:18]([N:20]4[CH2:21][CH2:22][N:23]([CH2:40][CH2:39][CH2:38][CH2:37][O:36][C:33](=[O:35])[CH3:34])[CH2:24][CH2:25]4)[CH:17]=[CH:16][CH:15]=3)[CH:5]=[CH:4][C:3]1=2

Participants

Conditions

Temperature: 50 °C

Procedure

100 mg (0.29 mmol) of 1-[6-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)pyridin-2-yl]piperazine are dissolved in 2 ml of DMF, and 47 mg (0.29 mmol) of potassium carbonate are added. 42 μl (0.29 mmol) of 4-bromobutyl acetate are subsequently added, and the mixture is stirred at 50° C. for 24 h. A further 11 μl (0.07 mmol) of 4-bromobutyl acetate are subsequently added, and the mixture is stirred at 50° C. for a further 48 h. The reaction mixture is evaporated, water is added to the residue, the mixture is rendered basic using 1 N NaOH and extracted three times with ethyl acetate. The organic phase is dried over Na2SO4 and evaporated. The crude product is purified by means of column chromatography on silica gel.

Workup

stirringthe mixture is stirred at 50° C. for a further 48 h
customThe reaction mixture is evaporated
additionwater is added to the residue
extractionextracted three times with ethyl acetate
dry with materialThe organic phase is dried over Na2SO4
customevaporated
customThe crude product is purified by means of column chromatography on silica gel

Sources & evidence

ORD record: ord-3d7212d96d384f13a972cb2312516170
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09062015B2

Reaction notes

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