Potassium Iodide → 1-Benzyl-5-(cyclooctyl-methyl)-spiro[indoline-3,4'-piperidin]-2-one

HRID 1441673Notes

Reaction equation

Br[CH2:2][CH:3]1[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.[CH2:11]([N:18]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[C:20]2([CH2:25][CH2:24][NH:23][CH2:22][CH2:21]2)[C:19]1=[O:32])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CN(C)C=O>[CH2:11]([N:18]1[C:31]2[C:26](=[CH:27][C:28]([CH2:2][CH:3]3[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]3)=[CH:29][CH:30]=2)[C:20]2([CH2:21][CH2:22][NH:23][CH2:24][CH2:25]2)[C:19]1=[O:32])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

Conditions

Temperature: 55 °C

Procedure

1-Bromomethyl-cyclooctane (0.087 g, 0.424 mmol) and 1-benzyl-spiro[indoline-3,4′-piperidin]-2-one (0.030 g, 0.141 mmol) were dissolved in dry N,N-dimethylformamide (3 mL). Potassium carbonate (0.078 g, 0.565 mmol) and a catalytic amount of potassium iodide were added. The reaction mixture was then stirred at 55° C. under nitrogen atmosphere for 18 hours. The reaction mixture was partitioned with water and ethyl acetate. The organic layer was washed with brine, dried with Na2SO4, filtered and the solvent evaporated in vacuo to yield a crude oil. The crude oil was purified via flash chromatography (50% ethyl acetate/hexanes) to yield the title compound as an oil.

Workup

customThe reaction mixture was partitioned with water and ethyl acetate
washThe organic layer was washed with brine
dry with materialdried with Na2SO4
filtrationfiltered
customthe solvent evaporated in vacuo
customto yield a crude oil
customThe crude oil was purified via flash chromatography (50% ethyl acetate/hexanes)

Sources & evidence

ORD record: ord-b60e0c43a94048c782d121424baf754a
Source dataset: uspto-grants-2010_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07655670B2

Reaction notes

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