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

HRID 266083

反応式

HRID 266083 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.[CH3:25][O:26][C:27]1[CH:32]=[CH:31][C:30]([CH2:33][CH2:34]Br)=[CH:29][CH:28]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=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]([CH2:34][CH2:33][C:30]2[CH:31]=[CH:32][C:27]([O:26][CH3:25])=[CH:28][CH:29]=2)[CH2:14][CH2:13]1)=[O:11]

参加物

6

反応物 4

HCID 6422Trifluoroacetic acidHCID 11430Potassium CarbonateHCID 844271-(2-Bromoethyl)-4-methoxybenzeneHCID 152370094-(Benzthiazole-2-carbonyl)piperidine

生成物 1

HCID 9842862[2-Benzothiazolyl][1-[2-(4-methoxyphenyl)ethyl]-4-piperidinyl)methanone

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

Mix (2-benzothiazolyl)(4-piperidinyl)methanone.CF3CO2H (331 g, 9.19 mmol), 2-(4-methoxyphenyl)ethyl bromide (2.07 g, 9.64 mmol), potassium carbonate (3.33 g, 24.1 mmol) and dimethylformamide (35 mL) and heat at 90° C. overnight. Cool to room temperature and partition between a 2:1 mixture of ethyl acetate/toluene and water. Separate the aqueous phase and wash the organic phase with water and brine. Dry (MgSO4) and evaporate the solvent in vacuo. Purify by chromatography (30% ethyl acetate/hexane) and recrystallize (cyclohexane) to give the title compound as a tan powder; mp 119°-120° C.

後処理

  1. custompartition between a 2:1 mixture of ethyl acetate/toluene and water
  2. customSeparate the aqueous phase
  3. washwash the organic phase with water and brine
  4. dry with materialDry (MgSO4)
  5. customevaporate the solvent in vacuo
  6. customPurify by chromatography (30% ethyl acetate/hexane)
  7. customrecrystallize (cyclohexane)

出典と根拠

ORDレコード
ord-966941741a354e3b8db2041c041f72b5
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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