1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 1-(4-Chlorobenzyl)-3-[(4-benzoylbutyryl)amino]homopiperidine

HRID 2187860Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2187860
[NH2:1][CH:2]1[CH2:8][CH2:7][CH2:6][CH2:5][N:4]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=2)[CH2:3]1.[C:17]([CH2:25][CH2:26][CH2:27][C:28](O)=[O:29])(=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1>C(Cl)(Cl)Cl.C(Cl)Cl.CCN(CC)CC>[Cl:16][C:13]1[CH:12]=[CH:11][C:10]([CH2:9][N:4]2[CH2:5][CH2:6][CH2:7][CH2:8][CH:2]([NH:1][C:28](=[O:29])[CH2:27][CH2:26][CH2:25][C:17](=[O:24])[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH2:3]2)=[CH:15][CH:14]=1

Komponenten

8

Edukt 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 73914delta-Oxobenzenepentanoic acidHCID 757711-HydroxybenzotriazoleHCID 184262393-Amino-1-(4-chlorobenzyl)homopiperidine

Produkt 1

HCID 98230081-(4-Chlorobenzyl)-3-[(4-benzoylbutyryl)amino]homopiperidine

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6212ChloroformLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 8471TriethylamineLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

A solution of 3-amino-1-(4-chlorobenzyl)homopiperidine (24 mg, 0.10 mmol) and 4-benzoylbutyric acid (1.2 equiv.) in CHCl3 (1 mL) was treated with EDCI (23 mg), HOBt (16.2 mg) and Et3N (15.2 μL), and stirred at 25° C. for 16 h. The reaction mixture was diluted with CH2Cl2 (0.5 mL), washed with 2 N aqueous NaOH solution (2×0.75 mL), dried by filtration through a PTFE membrane and concentrated to afford 1-(4-chlorobenzyl)-3-{(4-benzoylbutyryl)amino}homopiperidine (compound No. 994) (43 mg, 99%): The purity was determined by RPLC/MS (98%); ESI/MS m/e 413 (M++H, C24H29ClN2O2)

Aufarbeitung

  1. washwashed with 2 N aqueous NaOH solution (2×0.75 mL)
  2. dry with materialdried by filtration through a PTFE membrane
  3. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-3aabed5daecb4a00b10945951de35495
Quelldatensatz
uspto-grants-2002_06
Patentnummer
US06410566B1

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