Diisopropylethylamine → N-[1-(4-Chloro-3,5-diethoxy-benzyl)-piperidin-4-yl]-3-hydroxymethyl-5-methoxy-benzamide
Reaktionsgleichung
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:27]=[C:28]([O:31][CH2:32][CH3:33])[C:29]=1F)[CH2:7][N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15](=[O:26])[C:16]2[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[C:18]([CH2:24][OH:25])[CH:17]=2)[CH2:10][CH2:9]1)[CH3:2].[Cl:34]C1C(OCC)=CC(C=O)=CC=1OCC.C(OC(=O)C1C=C(OCC)C(Cl)=C(OCC)C=1)C.[H-].C([Al+]CC(C)C)C(C)C.C([BH3-])#N.[Na+].C(N(C(C)C)C(C)C)C>C(O)C.O=[Mn]=O.C(O)(=O)C>[Cl:34][C:29]1[C:4]([O:3][CH2:1][CH3:2])=[CH:5][C:6]([CH2:7][N:8]2[CH2:13][CH2:12][CH:11]([NH:14][C:15](=[O:26])[C:16]3[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[C:18]([CH2:24][OH:25])[CH:17]=3)[CH2:10][CH2:9]2)=[CH:27][C:28]=1[O:31][CH2:32][CH3:33]Komponenten
10
Edukt 6
HCID 81531Diisopropylethylamine
HCID 5003444Sodium cyanoborohydride
HCID 21225700Diisobutylaluminumhydride
HCID 592103754-Chloro-3,5-diethoxybenzaldehyde
HCID 596847734-Chloro-3,5-diethoxybenzoic acid ethyl ester
HCID 68458782N-[1-(3,5-Diethoxy-4-fluoro-benzyl)-piperidin-4-yl]-3-hydroxymethyl-5-methoxy-benzamideProdukt 1
Reagenzien, Katalysatoren, Lösungsmittel 3
Versuchsvorschrift
In analogy to the procedure described in example 50k), 3-hydroxymethyl-5-methoxy-N-piperidin-4-yl-benzamide (example 217) was reacted with 4-chloro-3,5-diethoxy-benzaldehyde [prepared from 4-chloro-3,5-diethoxy-benzoic acid ethyl ester (example 219a) by reduction with di-isobutylaluminium hydride followed by oxidation with MnO2 in analogy to the procedures described in example 1a)], sodium cyanoborohydride, N-ethyl-diisopropylamine and acetic acid in ethanol at 50° C. to yield the title compound as colorless oil. MS: 477.0 (MH+).
Aufarbeitung
- customat 50° C.
Quellen und Nachweise
- ORD-Eintrag
- ord-e98e0ed8fbc04ac0b8b417e58f2f167a
- Quelldatensatz
- uspto-grants-2010_08
- Patentnummer
- US07772253B2
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