Trifluoroacetic acid → [2-Benzothiazolyl][1-[2-(4-fluorophenyl)ethyl]-4-piperidinyl]methanone

HRID 1491680Notes

Reaction equation

HRID 1491680 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]([CH:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1)=[O:11].C(C(O)=O)(F)(F)F.[F:25][C:26]1[CH:31]=[CH:30][C:29]([CH2:32][CH2:33]Br)=[CH:28][CH:27]=1.[OH-].[Na+]>[Br-].C([N+](CC)(CC)CC)C1C=CC=CC=1.C(Cl)Cl.O>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]([CH:12]1[CH2:17][CH2:16][N:15]([CH2:33][CH2:32][C:29]2[CH:30]=[CH:31][C:26]([F:25])=[CH:27][CH:28]=2)[CH2:14][CH2:13]1)=[O:11]

Participants

8

Reactant 4

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 5731534-Fluorophenethyl bromideHCID 152370094-(Benzthiazole-2-carbonyl)piperidine

Product 1

HCID 15337459[2-Benzothiazolyl][1-[2-(4-fluorophenyl)ethyl]-4-piperidinyl]methanone

Reagents, catalysts & solvents 3

HCID 165294Benzyltriethylammonium bromideCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Mix (2-benzothiazolyl)(4-piperidinyl)methanone.CF3CO2H (1.95 g, 5.43 mmol), 2-(4-fluorophenyl)ethyl bromide (1.70 g, 8.35 mmol), benzyltriethylammonium bromide (149 mg, 0.54 mmol), sodium hydroxide (5 g), water (25 mL) and methylene chloride (25 mL). Stir at room temperature under an argon atmosphere overnight, then heat at reflux overnight. Cool the reaction to room temperature, separate the organic phase and extract the aqueous phase with methylene chloride (50 mL). Combine the organic phases, dry (Na2SO4) and evaporate the solvent in vacuo. Purify by chromatography (20% ethyl acetate/hexane with 2% triethylamine) and recrystallize (hexane) to give the title compound as pale yellow needles; mp 97°-98° C.

Workup

  1. temperatureheat
  2. temperatureat reflux overnight
  3. temperatureCool
  4. customthe reaction to room temperature
  5. customseparate the organic phase
  6. extractionextract the aqueous phase with methylene chloride (50 mL)
  7. dry with materialCombine the organic phases, dry (Na2SO4)
  8. customevaporate the solvent in vacuo
  9. customPurify by chromatography (20% ethyl acetate/hexane with 2% triethylamine)
  10. customrecrystallize (hexane)

Sources & evidence

ORD record
ord-44e721c7135940feb5e9950cdf519573
Source dataset
uspto-grants-1994_12
Patent number
US05371093

Reaction notes

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