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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
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1177878
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]
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Komponenten

8

Edukt 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

Produkt 1

HCID 59559677
1-(3-Phenyl-propyl)-piperidine-4-carboxylic acid {2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-amide
Ausbeute 59,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-843568053b4047938ff2373f54191aad
Quelldatensatz
uspto-grants-2010_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07842696B2

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