Hydrochloric Acid → HCID 66961098, compound

HRID 1446507Notes

Reaction equation

HRID 1446507 reaction equation
[CH3:1][N:2]([CH:4]=[O:5])[CH3:3].[H-].[Na+].ClC[C:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=[CH:12][CH:11]=1.Cl.[CH2:21]1[CH2:25]OC[CH2:22]1>[I-].[Na+]>[C:18]1([CH2:1][N:2]2[CH2:3][CH2:25][CH2:21][CH2:22][C:4]2=[O:5])[C:19]2[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:15]=[CH:16][CH:17]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 68451-ChloromethylnaphthaleneHCID 8028TetrahydrofuranHCID 24758Sodium hydride

Product 1

HCID 66961098HCID 66961098, compound

Reagents, catalysts & solvents 1

HCID 5238Sodium IodideCatalyst

Conditions

Temperature
60 °C

Procedure

To a DMF (20 mL) solution of 6-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

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

Sources & evidence

ORD record
ord-2c13ebe9b39e4e59894c990d1214ce79
Source dataset
uspto-grants-2010_02
Patent number
US07667041B2

Reaction notes

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