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1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 1-(3-Phenyl-propyl)-piperidine-4-carboxylic acid {2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-amide

HRID 1177878
ノート
印刷プレビュー

反応式

HRID 1177878 の反応式
CCN(C(C)C)C(C)C.[C:10]1([CH2:16][CH2:17][CH2:18][N:19]2[CH2:24][CH2:23][CH:22]([C:25]([OH:27])=O)[CH2:21][CH2:20]2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.FC(F)(F)C(O)=O.[NH2:56][CH2:57][C:58]([N:60]1[CH2:65][CH2:64][N:63]([C:66](=[O:77])[C:67]2[CH:72]=[CH:71][CH:70]=[CH:69][C:68]=2[C:73]([F:76])([F:75])[F:74])[CH2:62][CH2:61]1)=[O:59]>CN(C=O)C.O>[O:59]=[C:58]([N:60]1[CH2:61][CH2:62][N:63]([C:66](=[O:77])[C:67]2[CH:72]=[CH:71][CH:70]=[CH:69][C:68]=2[C:73]([F:76])([F:75])[F:74])[CH2:64][CH2:65]1)[CH2:57][NH:56][C:25]([CH:22]1[CH2:21][CH2:20][N:19]([CH2:18][CH2:17][CH2:16][C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:24][CH2:23]1)=[O:27]
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 176040671-(3-Phenylpropyl)piperidine-4-carboxylic acidHCID 866340882-amino-1-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethanone TFA salt

生成物 1

HCID 59559677
1-(3-Phenyl-propyl)-piperidine-4-carboxylic acid {2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-amide
収率 59.2%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

DIPEA (95.64 mg, 0.11 mL, 0.74 mmol) was added to a stirred solution of 1-(3-Phenyl-propyl)-piperidine-4-carboxylic acid (55.22 mg, 0.22 mmol) in DMF (1 mL). HOBT (30.19 mg, 0.22 mmol) and EDCI (42.74 mg, 0.22 mmol) were then added at room temperature. After 2 minutes, 2-amino-1-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethanone trifluoroacetic acid salt (80 mg, 0.18 mmol) was added and the resulting mixture was stirred at room temperature for 16 hrs. Cold water was then added and the product was extracted with EtOAc and the organic layer was washed with brine. The organic phase was dried over Na2SO4 and concentrated under reduced pressure to afford 58 mg (57.16% yield) of 1-(3-Phenyl-propyl)-piperidine-4-carboxylic acid {2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-amide. LCMS Purity: 95.21%. 1H NMR (CDCl3): δ 7.8-7.5 (d, 3H), 7.38-7.3 (s, 1H), 7.22-7.08 (s, 3H), 6.62-6.5 (s, 1H), 4.2-3.8 (m, 4H), 3.7-3.4 (m, 4H), 3.4-3.2 (m, 3H), 3.0 (s, 2H), 2.7-2.6 (s, 2H), 2.5-2.1 (m, 4H), 2.0-1.8 (m, 6H).

後処理

  1. extractionthe product was extracted with EtOAc
  2. washthe organic layer was washed with brine
  3. dry with materialThe organic phase was dried over Na2SO4
  4. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-843568053b4047938ff2373f54191aad
出典データセット
uspto-grants-2010_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07842696B2

反応ノート

読み込み中…

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