1-Chloro-2-(diethylamine)ethane hydrochloride → HCID 178464092, compound

HRID 25659

Reaction equation

HRID 25659 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([C@H:13]2[CH2:18][CH2:17][C@H:16]([OH:19])[CH2:15][CH2:14]2)[CH3:12])(=[O:10])=[O:9])=[CH:4][CH:3]=1.Cl.[CH2:21]([N:23]([CH2:27][CH3:28])[CH2:24][CH2:25]Cl)[CH3:22].[OH-].[Na+]>C1(C)C=CC=CC=1.[N+](CCCC)(CCCC)(CCCC)CCCC.[O-]S(O)(=O)=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([C@H:13]2[CH2:18][CH2:17][C@H:16]([O:19][CH2:22][CH2:21][N:23]([CH2:27][CH3:28])[CH2:24][CH3:25])[CH2:15][CH2:14]2)[CH3:12])(=[O:9])=[O:10])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 133631-Chloro-2-(diethylamine)ethane hydrochlorideHCID 14798Sodium HydroxideHCID 178484844HCID 178484844, compound

Product 1

HCID 178464092HCID 178464092, compoundYield 84.9%

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 1140TolueneSolvent

Procedure

To 350 mg (1 mmol) trans-4-Bromo-N-(4-hydroxy-cyclohexyl)-N-methyl-benzenesulfonamide in 6 ml toluene was added 344 mg (2.0 mmol) 2-diethylamino-ethylchlorid.hydrochloride and a catalytic amount of Bu4NHSO4 followed by 4 ml 50% NaOH. The mixture was stirred at RT over night, the phases were separated and the organic phase dried over Na2SO4. Column chromatography on silica gel with CH2Cl2/MeOH 15:1 yielded 380 mg (84%) trans-4-Bromo-N-[4-(2-diethylamino-ethoxy)-cyclohexyl]-N-methyl-benzenesulfonamide as light yellow oil, MS: 447 (MH+, 1Br).

Workup

  1. customthe phases were separated
  2. dry with materialthe organic phase dried over Na2SO4

Sources & evidence

ORD record
ord-e2e0ee6db3284bfbb9078e69bf09e43f
Source dataset
uspto-grants-2005_02
Patent number
US06858651B2

Linked notes

Loading…