Chloroform → (1-Methyl-7-methoxy-2,2-dimethyl-1,2,3,4-tetrahydroquinol-4-yl)-N-octyl-methane-sulfonamide

HRID 84147Notes

Reaction equation

HRID 84147 reaction equation
COC(C1CCN(S(C[C:15]2[C:24]3C(=[CH:20][CH:21]=[CH:22][CH:23]=3)[N:18](CC)[C:17](C)(C)[CH:16]=2)(=O)=O)CC1)=O.[CH3:29][N:30]1[C:39]2[C:34](=[CH:35][CH:36]=[C:37]([O:40][CH3:41])[CH:38]=2)[CH:33]([CH2:42][S:43](Cl)(=[O:45])=[O:44])[CH2:32][C:31]1([CH3:48])[CH3:47].C(N)CCCCCCC.C(Cl)(Cl)Cl>C(#N)C.C(O)C>[CH3:29][N:30]1[C:39]2[C:34](=[CH:35][CH:36]=[C:37]([O:40][CH3:41])[CH:38]=2)[CH:33]([CH2:42][S:43]([NH:18][CH2:17][CH2:16][CH2:15][CH2:24][CH2:23][CH2:22][CH2:21][CH3:20])(=[O:45])=[O:44])[CH2:32][C:31]1([CH3:48])[CH3:47]

Participants

7

Reactant 4

HCID 6212ChloroformHCID 8143OctylamineHCID 12138183(1-Ethyl-2,2-dimethyl-1,2-dihydroquinol-4-yl-methanesulfonyl)-piperidine-4-carboxylic acid methyl esterHCID 12138193(1-Methyl-7-methoxy-2,2-dimethyl-1,2,3,4-tetrahydroquinol-4-yl)-methane-sulfonic acid chloride

Product 1

HCID 12138195(1-Methyl-7-methoxy-2,2-dimethyl-1,2,3,4-tetrahydroquinol-4-yl)-N-octyl-methane-sulfonamideYield 69%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6342AcetonitrileSolvent

Procedure

(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.

Workup

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

Sources & evidence

ORD record
ord-c485fc9fd69d447d9cb1396e391677a2
Source dataset
uspto-grants-2014_09
Patent number
US08846924B2

Reaction notes

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