Methylamine → (Z)-4-(1-(4-(2-(methylamino)ethoxy)phenyl)-2-(1,4-dioxaspiro-[4.5]decan-8-yl)but-1-enyl)phenol

HRID 626182Notes

Reaction equation

Cl[CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8](/[C:11](/[C:25]2[CH:30]=[CH:29][C:28]([OH:31])=[CH:27][CH:26]=2)=[C:12](\[CH:15]2[CH2:24][CH2:23][C:18]3([O:22][CH2:21][CH2:20][O:19]3)[CH2:17][CH2:16]2)/[CH2:13][CH3:14])=[CH:7][CH:6]=1.[CH3:32][NH2:33]>CO>[CH3:32][NH:33][CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8](/[C:11](/[C:25]2[CH:30]=[CH:29][C:28]([OH:31])=[CH:27][CH:26]=2)=[C:12](\[CH:15]2[CH2:24][CH2:23][C:18]3([O:22][CH2:21][CH2:20][O:19]3)[CH2:17][CH2:16]2)/[CH2:13][CH3:14])=[CH:7][CH:6]=1

Participants

Conditions

Temperature: 85 °C

Procedure

A mixture of (Z)-4-(1-(4-(2-chloroethoxy)phenyl)-2-(1,4-dioxaspiro[4.5]decan-8-yl)but-1-enyl)phenol (90 mg, 0.20 mol), 30% aqueous of CH3NH2 (5 mL), and MeOH (5 mL) was heated at 85° C. in a sealed tube overnight, concentrated, and purified by column chromatography to give the desired product (90 mg).

Workup

concentrationconcentrated
custompurified by column chromatography

Sources & evidence

ORD record: ord-fd2565b8f94e4567acc46c2fc1678b5e
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09309211B2

Reaction notes

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