Reaction #54034

ord-327afb34ff494ccc98e407e845ba3144

Reaction equation

C=CCOCC1=CC(C)(C)Nc2ccc(-c3ccccc3OC)cc21
4-Allyloxymethyl-6-(2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinoline
COc1ccccc1-c1ccc2c(c1)C(CBr)=CC(C)(C)N2
4-bromomethyl-6-(2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinoline
C=CCO
allyl alcohol
C[Si](C)(C)[N-][Si](C)(C)C.[Na+]
sodium bis(trimethylsilyl)amide
→
COc1ccccc1-c1ccc2c(c1)C(CNc1ccccc1)=CC(C)(C)N2
title compound
COc1ccccc1-c1ccc2c(c1)C(CNc1ccccc1)=CC(C)(C)N2
[6-(2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinolin-4-ylmethyl]phenylamine

Reactants

—
solution
C=CCOCC1=CC(C)(C)Nc2ccc(-c3ccccc3OC)cc21
4-Allyloxymethyl-6-(2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinoline
COc1ccccc1-c1ccc2c(c1)C(CBr)=CC(C)(C)N2
4-bromomethyl-6-(2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinoline
C=CCO
allyl alcohol
C[Si](C)(C)[N-][Si](C)(C)C.[Na+]
sodium bis(trimethylsilyl)amide

Reagents

None

Solvents

C1CCOC1
THF

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Procedure

4-Allyloxymethyl-6-(2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinoline 40 mg of 4-bromomethyl-6-(2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinoline, 44 μL of allyl alcohol, and 4 mL of 1 M solution of sodium bis(trimethylsilyl)amide in THF reacted to give 4.5 mg of the title compound as a foam.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US06858627B2uspto-grants-2005_02