2-Naphthalenecarboxaldehyde → 4-Naphthalen-2-ylmethyl-piperazine-1-carboxylic acid phenylamide

HRID 40584

Reaktionsgleichung

Reaktionsgleichung von HRID 40584
[C:1]1([NH:7][C:8]([N:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:16]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:19]=[CH:18][C:17]=1[CH:26]=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].[OH-].[K+]>C(Cl)Cl>[C:1]1([NH:7][C:8]([N:10]2[CH2:15][CH2:14][N:13]([CH2:26][C:17]3[CH:18]=[CH:19][C:20]4[C:25](=[CH:24][CH:23]=[CH:22][CH:21]=4)[CH:16]=3)[CH2:12][CH2:11]2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Komponenten

6

Edukt 4

HCID 62012-NaphthalenecarboxaldehydeHCID 14797Potassium HydroxideHCID 5049666Sodium triacetoxyborohydrideHCID 7015289N-phenylpiperazine-1-carboxamide

Produkt 1

HCID 116673584-Naphthalen-2-ylmethyl-piperazine-1-carboxylic acid phenylamideAusbeute 64 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of piperazine-1-carboxylic acid phenylamide (103 mg) and 2-naphthaldehyde (94 mg) in DCM (2 mL) was treated with NaB(OAc)3H (148 mg). After 16 h, the resulting mixture was treated with 10% aq. KOH (2 mL). The aqueous phase was extracted with DCM (2×3 mL). The combined extracts were dried (MgSO4) and concentrated. Chromatography of the residue gave the title compound as a white foam (111 mg). 1H NMR (400 MHz, CDCl3): 7.85-7.80 (m, 3H), 7.74 (s, 1H), 7.52-7.45 (m, 3H), 7.35-7.25 (m, 4H), 7.05-7.00 (m, 1H), 6.37 (br s, 1H), 3.69 (s, 2H), 3.53-3.48 (m, 4H), 2.55-2.49 (m, 4H).

Aufarbeitung

  1. extractionThe aqueous phase was extracted with DCM (2×3 mL)
  2. dry with materialThe combined extracts were dried (MgSO4)
  3. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-bb4c30ad2997441bb4dbb53cd7b65c5c
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08530476B2

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