2,2,6-Trimethyl-4H-1,3-dioxin-4-one → HCID 117701834, compound

HRID 1751964Notes

Reaction equation

[CH3:1][N:2]([CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH:3]1[CH2:12][CH2:11][C:10]2[N:9]=[CH:8][C:7]([NH2:13])=[CH:6][C:5]=2[CH2:4]1.CC1(C)[O:28][C:27](=O)[CH:26]=[C:25]([CH3:30])[O:24]1>C1(C)C=CC=CC=1>[CH3:1][N:2]([CH2:14][CH2:15][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[CH:3]1[CH2:12][CH2:11][C:10]2[N:9]=[CH:8][C:7]([NH:13][C:27](=[O:28])[CH2:26][C:25](=[O:24])[CH3:30])=[CH:6][C:5]=2[CH2:4]1

Participants

Conditions

Temperature: 120 °C

Procedure

A 10 mL vial, equipped with a magnetic stirrer, was charged with N6-methyl-N6-(2-phenylethyl)-5,6,7,8-tetrahydroquinoline-3,6-diamine (79 mg, 0.281 mmol), 2,2,6-trimethyl-4H-1,3-dioxin-4-one (48 mg, 0.337 mmol), and toluene (3 mL). The vial was sealed and heated in a microwave reactor at 120° C. for 30 min. The reaction mixture was concentrated and the residue was purified by silica gel chromatography (0 to 100% acetone in hexanes) to give the title compound (73 mg, 71%). MS [M+H]+=366.2 m/z.

Workup

customA 10 mL vial, equipped with a magnetic stirrer
customThe vial was sealed
concentrationThe reaction mixture was concentrated
customthe residue was purified by silica gel chromatography (0 to 100% acetone in hexanes)

Sources & evidence

ORD record: ord-f7e2eba6e0b04bffbe12715d2e3288fa
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09162983B2

Reaction notes

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