2-(Ethylamino)ethanol → HCID 178464456, compound

HRID 25652Notes

Reaction equation

HRID 25652 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C@H:7]1[CH2:12][CH2:11][C@H:10]([NH:13][S:14]([C:17]2[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][CH:18]=2)(=[O:16])=[O:15])[CH2:9][CH2:8]1.[CH2:27]([NH:29][CH2:30][CH2:31][OH:32])[CH3:28].C([O-])(O)=O.[Na+]>CCO>[CH2:27]([N:29]([CH2:30][CH2:31][OH:32])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C@H:7]1[CH2:12][CH2:11][C@H:10]([NH:13][S:14]([C:17]2[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][CH:18]=2)(=[O:16])=[O:15])[CH2:9][CH2:8]1)[CH3:28]

Participants

5

Reactant 3

HCID 80722-(Ethylamino)ethanolHCID 516892Sodium BicarbonateHCID 178527576HCID 178527576, compound

Product 1

HCID 178464456HCID 178464456, compoundYield 80.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

A solution of 2.4 mg (5.26 mmol) of trans-N-[4-(5-Bromo-pentyl)-cyclohexyl]-4-trifluoromethyl-benzenesulfonamide in 36 ml of EtOH was treated with 2.1 ml (21.53 mmol) of ethyl-(2-hydroxy-ethyl)-amine, 1.8 g (21.43 mmol) of NaHCO3 and stirred over night at 90° C. The reaction cooled, filtered, evaporated and the residue extracted with aqueous saturated NaHCO3/EtOAc (3×). The organic phases were washed with aqueous 10% NaCl, dried (Na2SO4), filtered and evaporated. Purification by flash column chromatography on silica gel (EtOAc/EtOH/NH3 25% 98:2:1) gave 1.96 g (80%) of trans-N-(4-{5-[Ethyl-(2-hydroxy-ethyl)-amino]-pentyl}-cyclohexyl)-4-trifluoromethyl-benzenesulfonamide, MS: 463 (M−H−).

Workup

  1. temperatureThe reaction cooled
  2. filtrationfiltered
  3. customevaporated
  4. extractionthe residue extracted with aqueous saturated NaHCO3/EtOAc (3×)
  5. washThe organic phases were washed with aqueous 10% NaCl
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. customevaporated
  9. customPurification by flash column chromatography on silica gel (EtOAc/EtOH/NH3 25% 98:2:1)

Sources & evidence

ORD record
ord-c5d1e7d215684b1bbcd3f8bd2d6edd61
Source dataset
uspto-grants-2005_02
Patent number
US06858651B2

Reaction notes

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