Triethylamine → 4-[3-(Nonylcarbamoyloxy)-propylcarbamoyloxy]-piperidine-1-carboxylic acid 4-phenoxyphenyl ester

HRID 618291

Reaktionsgleichung

Reaktionsgleichung von HRID 618291
[O:1]([C:8]1[CH:13]=[CH:12][C:11]([O:14][C:15]([N:17]2[CH2:22][CH2:21][CH:20]([O:23][C:24](=[O:43])[NH:25][CH2:26][CH2:27][CH2:28][O:29][C:30](=[O:42])NOC3C=CC([N+]([O-])=O)=CC=3)[CH2:19][CH2:18]2)=[O:16])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:44]([NH2:53])[CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH3:52].C(N(CC)CC)C>CN(C)C=O.C(OCC)(=O)C>[O:1]([C:8]1[CH:13]=[CH:12][C:11]([O:14][C:15]([N:17]2[CH2:22][CH2:21][CH:20]([O:23][C:24](=[O:43])[NH:25][CH2:26][CH2:27][CH2:28][O:29][C:30](=[O:42])[NH:53][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH3:52])[CH2:19][CH2:18]2)=[O:16])=[CH:10][CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 16215NonylamineHCID 15463333HCID 15463333, Verbindung

Produkt 1

HCID 867544994-[3-(Nonylcarbamoyloxy)-propylcarbamoyloxy]-piperidine-1-carboxylic acid 4-phenoxyphenyl esterAusbeute 97,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of the carbonate (2.0 g, 3.4 mmol) produced in Example 17 in 20 mL of anhydrous dimethylformamide was added dropwise under nitrogen to a solution of nonylamine (760 μl, 4.1 mmol) and triethylamine (2.4 mL, 17 mmol) in 20 mL of anhydrous dimethylformamide at ice bath temperature. After the addition the solution was stirred at ice bath temperature for 2 hrs and at room temperature overnight. The reaction was diluted with ethyl acetate, extracted five times with water, one time with 1N HCl, five times with saturated Na2CO3, dried (MgSO4) and the solvent removed under reduced pressure to give 1.94 g of an off-white solid. Recrystallization from diisopropyl ether gave 1.55 g (77%) of the title compound as a white crystalline solid, mp 89-91° C.

Aufarbeitung

  1. additionAfter the addition the solution
  2. customat room temperature
  3. customovernight
  4. extractionextracted five times with water, one time with 1N HCl, five times with saturated Na2CO3
  5. dry with materialdried (MgSO4)
  6. customthe solvent removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-60580d1b0fee4618976546379b8a24ce
Quelldatensatz
uspto-grants-1999_09
Patentnummer
US05952354

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