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

HRID 266084

반응식

HRID 266084 반응식
[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]

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 165294Benzyltriethylammonium bromide촉매HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-2986c784a7864d1d83e439765f4be730
출처 데이터셋
uspto-grants-1997_07
특허 번호
US05650416

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