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

HRID 266084

反応式

HRID 266084 の反応式
[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]

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 165294Benzyltriethylammonium bromide触媒HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-2986c784a7864d1d83e439765f4be730
出典データセット
uspto-grants-1997_07
特許番号
US05650416

関連ノート

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