Acetone → N-[4-(2-methyl-2H-tetrazol-5-yl)phenylmethyl]-4-[bis(4-trifluoromethoxyphenyl)hydroxymethyl]piperidine

HRID 378512

Reaktionsgleichung

Reaktionsgleichung von HRID 378512
[CH3:1][N:2]1[N:6]=[N:5][C:4]([C:7]2[CH:12]=[CH:11][C:10]([CH2:13]Br)=[CH:9][CH:8]=2)=[N:3]1.[F:15][C:16]([F:44])([F:43])[O:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]([C:32]2[CH:37]=[CH:36][C:35]([O:38][C:39]([F:42])([F:41])[F:40])=[CH:34][CH:33]=2)([OH:31])[CH:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)=[CH:20][CH:19]=1.C(N(CC)C(C)C)(C)C.CC(C)=O>CS(C)=O.C(Cl)Cl>[CH3:1][N:2]1[N:6]=[N:5][C:4]([C:7]2[CH:12]=[CH:11][C:10]([CH2:13][N:28]3[CH2:29][CH2:30][CH:25]([C:24]([C:21]4[CH:20]=[CH:19][C:18]([O:17][C:16]([F:15])([F:43])[F:44])=[CH:23][CH:22]=4)([C:32]4[CH:37]=[CH:36][C:35]([O:38][C:39]([F:42])([F:41])[F:40])=[CH:34][CH:33]=4)[OH:31])[CH2:26][CH2:27]3)=[CH:9][CH:8]=2)=[N:3]1

Komponenten

7

Edukt 4

HCID 180AcetoneHCID 81531DiisopropylethylamineHCID 5893295-(4-Bromomethylphenyl)-2-methyl-2H-tetrazoleHCID 190409264-[Bis(4-trifluoromethoxyphenyl)hydroxymethyl]piperidine

Produkt 1

HCID 15515185N-[4-(2-methyl-2H-tetrazol-5-yl)phenylmethyl]-4-[bis(4-trifluoromethoxyphenyl)hydroxymethyl]piperidineAusbeute 32,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

This compound was prepared in a manner analogous to that of Step D of Example 4, with 0.3 gram (0.001 mole) of 4-(2-methyl-2H-tetrazol-5-yl)phenylmethyl bromide, 0.5 gram (0.001 mole) of 4-[bis(4-trifluoromethoxyphenyl)hydroxymethyl]piperidine (prepared as in Step C of Example 4), and 0.6 gram (0.004 mole) of N, N-diisopropylethylamine in about 5 mL of dimethyl sulfoxide as reagents. The crude reaction product was subjected to column chromatography on silica gel, with 3:7 acetone:methylene chloride as the eluant. The product-containing fractions were combined and concentrated under reduced pressure, yielding about 0.2 gram of N-[4-(2-methyl-2H-tetrazol-5-yl)phenylmethyl]-4-[bis(4-trifluoromethoxyphenyl)hydroxymethyl]piperidine. The NMR spectrum was consistent with the proposed structure.

Aufarbeitung

  1. customThis compound was prepared in a manner analogous to that of Step D of Example 4
  2. customThe crude reaction product
  3. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-bcb5a56cc3a54c96b180134c7064c21f
Quelldatensatz
uspto-grants-2000_02
Patentnummer
US06030987

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