(Diethylamino)sulfur trifluoride → HCID 18516087, compound

HRID 1790486Notes

Reaction equation

HRID 1790486 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8](O)[CH2:9][N:10]2[CH2:15][CH2:14][CH:13]([N:16]3[C:25]4[C:20](=[CH:21][CH:22]=[C:23]([O:26][CH3:27])[CH:24]=4)[CH2:19][CH2:18][CH2:17]3)[CH2:12][CH2:11]2)=[CH:4][CH:3]=1.C(N(S(F)(F)[F:35])CC)C.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([F:35])[CH2:9][N:10]2[CH2:11][CH2:12][CH:13]([N:16]3[C:25]4[C:20](=[CH:21][CH:22]=[C:23]([O:26][CH3:27])[CH:24]=4)[CH2:19][CH2:18][CH2:17]3)[CH2:14][CH2:15]2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 123472(Diethylamino)sulfur trifluorideHCID 516892Sodium BicarbonateHCID 22038239HCID 22038239, compound

Product 1

HCID 18516087HCID 18516087, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1-{1-[2-(4-fluorophenyl)-2-hydroxyethyl]piperidin-4-yl}-7-methoxy-1,2,3,4-tetrahydroquinoline (250 mg) in methylene chloride (5 ml) was cooled to −78° C. and diethylaminosulfur trifluoride (DAST, 0.1 ml) was added thereto. Then the reaction solution was stirred at the same temperature for 45 min. After the completion of the reaction, saturated sodium bicarbonate was added to the reaction solution, which was then allowed to warm to room temperature under stirring. The reaction solution was extracted with ethyl acetate and the organic layer was dried over magnesium sulfate. After evaporating the solvent, the resulting residue was purified by silica gel column chromatography (hexane/hexane system) to give 1-{1-[2-(4-fluorophenyl)-2-fluoroethyl]piperidin-4-yl}-7-methoxy-1,2,3,4-tetrahydroquinoline as an oil. This product was dissolved in ethyl acetate. After adding hydrochloric acid, the resulting salt was recrystallized from ethanol/ether to give the title compound (60 mg) (yield: 24%).

Workup

  1. additionwas added to the reaction solution, which
  2. stirringunder stirring
  3. extractionThe reaction solution was extracted with ethyl acetate
  4. dry with materialthe organic layer was dried over magnesium sulfate
  5. customAfter evaporating the solvent
  6. customthe resulting residue was purified by silica gel column chromatography (hexane/hexane system)

Sources & evidence

ORD record
ord-6ebdcd3a48c84691bfcbe0f713571386
Source dataset
uspto-grants-2006_07
Patent number
US07071201B2

Reaction notes

Loading…