3-Hydroxybenzaldehyde → 4-(3-hydroxybenzyl)-N-phenylpiperazine-1-carboxamide

HRID 40580

Reaktionsgleichung

Reaktionsgleichung von HRID 40580
[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.[OH:16][C:17]1[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=1)[CH:20]=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].[OH-].[Na+].Cl>C(Cl)Cl.C(O)(=O)C>[C:1]1([NH:7][C:8]([N:10]2[CH2:15][CH2:14][N:13]([CH2:20][C:19]3[CH:22]=[CH:23][CH:24]=[C:17]([OH:16])[CH:18]=3)[CH2:12][CH2:11]2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Komponenten

8

Edukt 5

HCID 1013-HydroxybenzaldehydeHCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 5049666Sodium triacetoxyborohydrideHCID 7015289N-phenylpiperazine-1-carboxamide

Produkt 1

HCID 511062294-(3-hydroxybenzyl)-N-phenylpiperazine-1-carboxamideAusbeute 82,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of piperazine-1-carboxylic acid phenylamide (2.0 g) and 3-hydroxybenzaldehyde (3.0 g) in DCM (200 mL) was added acetic acid (1.1 mL) followed by portion-wise addition of NaB(OAc)3H (6.0 g). The reaction mixture was stirred overnight. A solution of 10% aq. NaOH (30 mL) was added until the pH of the aqueous phase was 11. A solution of 1 N HCl was then added until the pH of the aqueous phase was 6-7. The aqueous phase was extracted with DCM (200 mL). The combined organic layers were dried (MgSO4) and concentrated. Chromatography of the residue gave the title compound as a white solid (2.5 g).

Aufarbeitung

  1. extractionThe aqueous phase was extracted with DCM (200 mL)
  2. dry with materialThe combined organic layers were dried (MgSO4)
  3. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-9a9aff686fef4838ae9773244815ad90
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08530476B2

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