Piperidine → cis-3-(3-Piperidin-1-yl-indan-1-yl)-1H-indole

HRID 1435777Notes

Reaction equation

C([BH3-])#N.[Na+].[NH:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]([CH:14]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:16](=O)[CH2:15]2)=[CH:6]1.[NH:24]1[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1.[OH-].[Na+]>CO.C(O)(=O)C.O>[N:24]1([C@@H:16]2[C:17]3[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=3)[C@H:14]([C:7]3[C:8]4[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=4)[NH:5][CH:6]=3)[CH2:15]2)[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1

Participants

Conditions

Temperature: 150 °C

Procedure

Sodium cyanoborohydride (61 mg; 0.97 mmol ) was added to 3-(1H-indol-3-yl)-indan-1-one (200 mg; 0.81 mmol ) and piperidine (344 mg; 4.05 mmol ) in 3 mL methanol and 0.5 mL acetic acid. The reaction mixture was stirred 30 minutes at 150° C. under microwave irradiation using the Emry Optimizer™ instrument. The reaction mixture was poured into water and made basic with 27% aqueous NaOH. The mixture was extracted with ethyl acetate. The organic phase was dried over MgSO4 and concentrated in vacuo. cis-3-(3-Piperidin-1-yl-indan-1-yl)-1H-indole was obtained after flash chromatography (ethyl acetate, heptane, triethylamine, silica gel).

Workup

extractionThe mixture was extracted with ethyl acetate
dry with materialThe organic phase was dried over MgSO4
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-d9eaab6b4ecf4717946681f7ba4ba03a
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07618967B2

Reaction notes

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