Cyclohexanone → HCID 178443965, compound

HRID 230386Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]([C:8]2[N:9]=[C:10]([CH:13]([NH2:20])[CH2:14][CH2:15][CH2:16][CH:17]([CH3:19])[CH3:18])[NH:11][CH:12]=2)[CH:5]=[CH:6][CH:7]=1.C(N(CC)CC)C.[C:28]1(=O)[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CO.O>[Br:1][C:2]1[CH:3]=[C:4]([C:8]2[N:9]=[C:10]([CH:13]([NH:20][CH:28]3[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]3)[CH2:14][CH2:15][CH2:16][CH:17]([CH3:18])[CH3:19])[NH:11][CH:12]=2)[CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 23 °C

Procedure

A mixture containing 1-(4-(3-bromophenyl)-1H-imidazol-2-yl)-5-methyl-1-hexanamine (obtained at stage 13777.3; 0.8 g; 0.0019 mol), triethylamine (0.4 ml; 0.003 mol) and cyclohexanone (0.32 ml; 0.0023 mol) in 10 ml methanol was agitated for about 30 minutes at about 23° C. Sodium triacetoxyborohydride (630 mg; 0.003 mol) was then added. The reaction mixture was agitated for about 16 hours and then poured into water. After extraction with ethyl acetate, the organic phase was washed with a saturated sodium chloride solution and then dried over magnesium sulfate. The solvent was evaporated and the residue purified over a silica column (eluent mixture CH2Cl2-MeOH/95-05). A white-colored powder was obtained with a yield of 38%. Melting point: 236-238° C. MH+=418.2.

Workup

stirringThe reaction mixture was agitated for about 16 hours
extractionAfter extraction with ethyl acetate
washthe organic phase was washed with a saturated sodium chloride solution
dry with materialdried over magnesium sulfate
customThe solvent was evaporated
customthe residue purified over a silica column (eluent mixture CH2Cl2-MeOH/95-05)
customA white-colored powder was obtained with a yield of 38%

Sources & evidence

ORD record: ord-e25a6169f4c14e3893a35091db70428b
Source dataset: uspto-grants-2009_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07566734B2

Reaction notes

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