Morpholine → {4-[2-(3-Oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]piperazin-1-yl}methylindane-4-carbonitrile

HRID 1519602Notes

Reaction equation

[N:1]1([CH2:7][CH:8]2[C:16]3[CH:15]=[CH:14][CH:13]=[C:12]([C:17]#[N:18])[C:11]=3[CH2:10][CH2:9]2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.Br[CH2:20][CH2:21][C:22]1[CH:31]=[CH:30][C:25]2[C:26](=O)[O:27][CH2:28][C:24]=2[CH:23]=1.N1CC[O:35]CC1>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C=O)C>[O:35]=[C:28]1[C:24]2[CH:23]=[C:22]([CH2:21][CH2:20][N:4]3[CH2:3][CH2:2][N:1]([CH2:7][CH:8]4[C:16]5[CH:15]=[CH:14][CH:13]=[C:12]([C:17]#[N:18])[C:11]=5[CH2:10][CH2:9]4)[CH2:6][CH2:5]3)[CH:31]=[CH:30][C:25]=2[CH2:26][O:27]1

Participants

Conditions

Temperature: 60 °C

Procedure

To a flask containing 1-(piperazin-1-ylmethyl)-2,3-dihydro-1H-indene-4-carbonitrile (0.04 g, 0.17 mmol) was added 5-(2-bromoethyl)-2-benzofuran-1-(3H)-one (0.02 g, 0.06 mmol), tetrabutyl ammonium iodide (0.02 g, 0.06 mmol) and morpholine (0.08 mL, 0.99 mmol); the resulting mixture was dissolved in DMF (3 mL) and stirred at 60° C. Analysis of the reaction mixture indicated that reaction had gone to completion. The solution was concentrated in vacuo and shot into Mass-directed HPLC for separation to give the desired 1-({4-[2-(3-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]piperazin-1-yl}methyl)indane-4-carbonitrile. LC-MS (IE, m/z): 402 [M+1]+. (0.27 μM)

Workup

customAnalysis of the reaction mixture indicated that reaction
concentrationThe solution was concentrated in vacuo
customshot into Mass-directed HPLC for separation

Sources & evidence

ORD record: ord-d7e4ec1f10b540648c4776bfd43dd701
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09073882B2

Reaction notes

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