Diisopropylethylamine → {4-[(4-Benzyloxy-phenyl)-(3-methyl-but-2-enyl)-amino]-piperidin-1-yl}-[1-(3-methyl-butyl)-piperidin-4-yl]-methanone

HRID 1069181Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1069181
[CH3:1][CH:2]([CH3:14])[CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][CH:8]([C:11]([OH:13])=O)[CH2:7][CH2:6]1.[CH2:15]([O:22][C:23]1[CH:28]=[CH:27][C:26]([N:29]([CH2:36][CH:37]=[C:38]([CH3:40])[CH3:39])[CH:30]2[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]2)=[CH:25][CH:24]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(N(C(C)C)CC)(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.CCOC(C)=O>[CH2:15]([O:22][C:23]1[CH:28]=[CH:27][C:26]([N:29]([CH2:36][CH:37]=[C:38]([CH3:40])[CH3:39])[CH:30]2[CH2:35][CH2:34][N:33]([C:11]([CH:8]3[CH2:7][CH2:6][N:5]([CH2:4][CH2:3][CH:2]([CH3:1])[CH3:14])[CH2:10][CH2:9]3)=[O:13])[CH2:32][CH2:31]2)=[CH:25][CH:24]=1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Komponenten

7

Edukt 4

HCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 10641624(4-Benzyloxy-phenyl)-(3-methyl-but-2-enyl)-piperidin-4-yl-amineHCID 167689871-(3-Methylbutyl)piperidine-4-carboxylic acid

Produkt 1

HCID 9958704{4-[(4-Benzyloxy-phenyl)-(3-methyl-but-2-enyl)-amino]-piperidin-1-yl}-[1-(3-methyl-butyl)-piperidin-4-yl]-methanoneAusbeute 18 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

The preparation of Example 13: 1-(3-Methyl-butyl)-piperidine-4-carboxylic acid (0.1 g, 0.50 mmol) was dissolved in DMF (5 mL) and treated with (4-Benzyloxy-phenyl)-(3-methyl-but-2-enyl)-piperidin-4-yl-amine (0.175 g, 0.50 mmol), diisopropylethylamine (0.26 mL, 1.5 mmol), and HBTU (0.19 g, 0.50 mmol). The reaction was stirred for 4 hours, then diluted with EtOAc (125 mL), washed with saturated sodium bicarbonate solution and brine, dried over Na2SO4, and concentrated. The residue was chromatographed on silica gel eluting with 8% MeOH/CH2Cl2 to give 47 mg (18%) of {4-[(4-Benzyloxy-phenyl)-(3-methyl-but-2-enyl)-amino]-piperidin-1-yl }-[1-(3-methyl-butyl)-piperidin-4-yl]-methanone.

Aufarbeitung

  1. customThe preparation of Example 13
  2. washwashed with saturated sodium bicarbonate solution and brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customThe residue was chromatographed on silica gel eluting with 8% MeOH/CH2Cl2

Quellen und Nachweise

ORD-Eintrag
ord-b7e4b4b82fd3437ca2865f199df2ef99
Quelldatensatz
uspto-grants-2001_06
Patentnummer
US06251919B1

Notizen zur Reaktion

Wird geladen…