Chloroform → (1-Ethyl-2,2-dimethyl-1,2-dihydroquinol-4-yl)-N-octyl-methanesulfonamide

HRID 575511Notes

Reaction equation

HRID 575511 reaction equation
COC([CH:5]1[CH2:10][CH2:9][N:8]([S:11]([CH2:14][C:15]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[N:18]([CH2:25][CH3:26])[C:17]([CH3:28])([CH3:27])[CH:16]=2)(=[O:13])=[O:12])[CH2:7][CH2:6]1)=O.C(N1C2C(=CC=CC=2)C(CS(Cl)(=O)=O)=[CH:33][C:32]1(C)[CH3:46])C.C(N)CCCCCCC.C(Cl)(Cl)Cl>C(O)C>[CH2:25]([N:18]1[C:19]2[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:15]([CH2:14][S:11]([NH:8][CH2:7][CH2:6][CH2:5][CH2:10][CH2:9][CH2:33][CH2:32][CH3:46])(=[O:12])=[O:13])=[CH:16][C:17]1([CH3:28])[CH3:27])[CH3:26]

Participants

6

Reactant 4

HCID 6212ChloroformHCID 8143OctylamineHCID 12138182HCID 12138182, compoundHCID 12138183(1-Ethyl-2,2-dimethyl-1,2-dihydroquinol-4-yl-methanesulfonyl)-piperidine-4-carboxylic acid methyl ester

Product 1

HCID 12138188(1-Ethyl-2,2-dimethyl-1,2-dihydroquinol-4-yl)-N-octyl-methanesulfonamideYield 81%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(1-Ethyl-2,2-dimethyl-1,2-dihydroquinol-4-yl)-N-octyl-methanesulfonamide (12) is prepared similarly to compound (10) using compound (9) with n-octylamine. The product is isolated by column chromatography on silica gel with a gradient running from chloroform to ethanol.

Workup

  1. customThe product is isolated by column chromatography on silica gel with a gradient

Sources & evidence

ORD record
ord-c6d1e24b56544e20805d969f7d238dd7
Source dataset
uspto-grants-2015_05
Patent number
US09035042B2

Reaction notes

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