Hydrochloric Acid → HCID 66961098, compound

HRID 1362651Notes

Reaction equation

[C:1]1(=[O:7])[NH:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].Cl[CH2:11][C:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14][CH:13]=1.Cl>[I-].[Na+].C1COCC1.CN(C=O)C>[C:12]1([CH2:11][N:6]2[CH2:5][CH2:4][CH2:3][CH2:2][C:1]2=[O:7])[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14][CH:13]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a DMF (20 mL) solution of δ-valerolactam (1.0 g), sodium hydride (404 mg), 1-(chloromethyl)naphthalene (1.78 g) and sodium iodide (151 mg) were added one by one at 0° C., and the reaction solution was allowed to be warmed to 60° C., and was agitated for 6 hours. 2N hydrochloric acid and THF were added to the reaction solution, and the organic layer was partitioned. After the obtained organic layer was washed with a saturated saline solution, it was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel chromatography (heptane: elution solvent; ethyl acetate=1:2->ethyl acetate), and 2.42 g of the title compound was obtained. The physical properties of the compound are as follows.

Workup

customthe organic layer was partitioned
washAfter the obtained organic layer was washed with a saturated saline solution, it
dry with materialwas dried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel chromatography (heptane: elution solvent; ethyl acetate=1:2->ethyl acetate)

Sources & evidence

ORD record: ord-38ffbe39e9d9427290820b1eaa6aa956
Source dataset: uspto-grants-2011_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07880009B2

Reaction notes

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