Reaktion #171329

ord-c485fc9fd69d447d9cb1396e391677a2

Reaktionsgleichung

ClC(Cl)Cl
chloroform
CCN1c2ccccc2C(CS(=O)(=O)N2CCC(C(=O)OC)CC2)=CC1(C)C
compound ( 10 )
CCN1c2ccccc2C(CS(=O)(=O)N2CCC(C(=O)OC)CC2)=CC1(C)C
(1-ethyl-2,2-dimethyl-1,2-dihydroquinol-4-yl-methanesulfonyl)-piperidine-4-carboxylic acid methyl ester
COc1ccc2c(c1)N(C)C(C)(C)CC2CS(=O)(=O)Cl
compound ( 19 )
COc1ccc2c(c1)N(C)C(C)(C)CC2CS(=O)(=O)Cl
(1-Methyl-7-methoxy-2,2-dimethyl-1,2,3,4-tetrahydroquinol-4-yl)-methane-sulfonic acid chloride
CCCCCCCCN
n-octylamine
→
CCCCCCCCNS(=O)(=O)CC1CC(C)(C)N(C)c2cc(OC)ccc21
(1-Methyl-7-methoxy-2,2-dimethyl-1,2,3,4-tetrahydroquinol-4-yl)-N-octyl-methane-sulfonamide
Ausbeute 69.0%

Edukte

ClC(Cl)Cl
chloroform
CCN1c2ccccc2C(CS(=O)(=O)N2CCC(C(=O)OC)CC2)=CC1(C)C
compound ( 10 )
CCN1c2ccccc2C(CS(=O)(=O)N2CCC(C(=O)OC)CC2)=CC1(C)C
(1-ethyl-2,2-dimethyl-1,2-dihydroquinol-4-yl-methanesulfonyl)-piperidine-4-carboxylic acid methyl ester
COc1ccc2c(c1)N(C)C(C)(C)CC2CS(=O)(=O)Cl
compound ( 19 )
COc1ccc2c(c1)N(C)C(C)(C)CC2CS(=O)(=O)Cl
(1-Methyl-7-methoxy-2,2-dimethyl-1,2,3,4-tetrahydroquinol-4-yl)-methane-sulfonic acid chloride
CCCCCCCCN
n-octylamine

Reagenzien

Keine

Lösungsmittel

CCO
ethanol
CC#N
acetonitrile

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    SonstigeIt is isolated by column chromatography on silica gel using a gradient

Vorschrift

(1-Methyl-7-methoxy-2,2-dimethyl-1,2,3,4-tetrahydroquinol-4-yl)-N-octyl-methane-sulfonamide (21) is prepared similarly to compound (10) from compound (19) and n-octylamine in dry acetonitrile. It is isolated by column chromatography on silica gel using a gradient running from chloroform to ethanol.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08846924B2uspto-grants-2014_09