Water → 1-benzyl-2-(6-methoxy-2-naphthyl)-3-pentyl-1H-indole

HRID 2252958Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([C:13](=O)[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[CH:7]=[CH:6]2.Cl.[CH2:22]([N:29]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)N)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.O>C(O)C.CCCCCCC>[CH2:22]([N:29]1[C:31]2[C:36](=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:14]([CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])=[C:13]1[C:8]1[CH:7]=[CH:6][C:5]2[C:10](=[CH:11][CH:12]=[C:3]([O:2][CH3:1])[CH:4]=2)[CH:9]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

Conditions

Temperature: 10 °C

Procedure

Generally, a suspension of equimolar amounts of 1-(6-methoxynaphthalen-2-yl)heptan-1-one and N-benzyl-N-phenylhydrazine hydrochloride (BPH) in ethanol is heated under reflux for five hours. Two portions of 0.1 equivalent of BPH in ethanol are added to the suspension at one hour intervals. Alternatively, the solution of BPH in ethanol is added to reaction mixture continuously. The resulting mixture is refluxed for an hour, diluted with heptane, and treated with water at 45° C. The organic and aqueous phases are separated, and the organic phase is washed with water and cooled to 10° C. to initiate crystallization. Upon cooling to −15° C., 80%-85% of crystalline 1-benzyl-2-(6-methoxy-naphthalen-2-yl)-3-pentyl-1H-indole is obtained.

Workup

temperatureis heated
temperatureunder reflux for five hours
temperatureThe resulting mixture is refluxed for an hour
customThe organic and aqueous phases are separated
washthe organic phase is washed with water
customcrystallization
temperatureUpon cooling to −15° C.

Sources & evidence

ORD record: ord-1367d705423b450a9cedaa1405666a83
Source dataset: uspto-grants-2008_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07323483B2

Reaction notes

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