Water → 1'-(3,4-Dihydroquinolin-1(2h)-ylcarbonyl)spiro[indene-1,4'-piperidine]

HRID 551782Notes

Reaction equation

[N:1]1([C:11]([O:13]C2C=CC([N+]([O-])=O)=CC=2)=O)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.[CH2:23]1[C:28]2([C:36]3[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=3)[CH:30]=[CH:29]2)[CH2:27][CH2:26][NH:25][CH2:24]1.Cl.C(N(CC)CC)C.O>ClCCl>[N:1]1([C:11]([N:25]2[CH2:26][CH2:27][C:28]3([C:36]4[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=4)[CH:30]=[CH:29]3)[CH2:23][CH2:24]2)=[O:13])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1

Participants

Conditions

Temperature: 150 °C

Procedure

0.4 g of 4-nitrophenyl 3,4-dihydroquinoline-1(2H)-carboxylate, 0.357 g of 4-spiroindene-piperidine hydrochloride, 0.28 ml of triethylamine and 2 ml of water are introduced into a 10 ml glass tube. The tube is sealed and then heated at 150° C. under microwave irradiation for 50 minutes. Dichloromethane is added. The organic phase is dried over magnesium sulfate and the solvent is evaporated under reduced pressure. The residue is chromatographed on silica gel with a heptane/ethyl acetate gradient from 9/1 to 0/1. 0.393 g of 1′-(3,4-dihydroquinolin-1(2H)-ylcarbonyl)spiro[indene-1,4′-piperidine] is obtained.

Workup

customThe tube is sealed
dry with materialThe organic phase is dried over magnesium sulfate
customthe solvent is evaporated under reduced pressure
customThe residue is chromatographed on silica gel with a heptane/ethyl acetate gradient from 9/1 to 0/1

Sources & evidence

ORD record: ord-73587889789f4756bf820f8e03d376bf
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07947834B2

Reaction notes

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