Sodium triacetoxyborohydride → 4-[(4-tert-Butylmorpholin-2-yl)methyl]-N-(3,4-dichlorophenyl)piperazine-1-carboxamide

HRID 603256

Reaktionsgleichung

Reaktionsgleichung von HRID 603256
[C:1]([N:5]1[CH2:10][CH2:9][O:8][CH:7]([CH:11]=O)[CH2:6]1)([CH3:4])([CH3:3])[CH3:2].[Cl:13][C:14]1[CH:15]=[C:16]([NH:21][C:22]([N:24]2[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]2)=[O:23])[CH:17]=[CH:18][C:19]=1[Cl:20].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[C:1]([N:5]1[CH2:10][CH2:9][O:8][CH:7]([CH2:11][N:27]2[CH2:26][CH2:25][N:24]([C:22]([NH:21][C:16]3[CH:17]=[CH:18][C:19]([Cl:20])=[C:14]([Cl:13])[CH:15]=3)=[O:23])[CH2:29][CH2:28]2)[CH2:6]1)([CH3:2])([CH3:3])[CH3:4]

Komponenten

5

Edukt 3

HCID 5049666Sodium triacetoxyborohydrideHCID 16775732N-(3,4-Dichlorophenyl)piperazine-1-carboxamideHCID 576569134-Tert-butylmorpholine-2-carbaldehyde

Produkt 1

HCID 576567394-[(4-tert-Butylmorpholin-2-yl)methyl]-N-(3,4-dichlorophenyl)piperazine-1-carboxamideAusbeute 19,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of 4-tert-butylmorpholine-2-carbaldehyde (154 mg) and N-(3,4-dichlorophenyl)piperazine-1-carboxamide (247 mg) in dichloromethane (20 mL) was stirred at room temperature under argon. Sodium triacetoxyborohydride (381 mg) was added and the mixture was stirred overnight. The reaction was quenched with water and partitioned between water and dichloromethane. The organic layer was washed with saturated aqueous sodium hydrogen carbonate and then brine, dried (Na2SO4), filtered and concentrated. The residue was purified on the Isco™ Companion (12 g column: 0-11% MeOH in DCM) to give the title compound as a white solid (75 mg).

Aufarbeitung

  1. customThe reaction was quenched with water
  2. custompartitioned between water and dichloromethane
  3. washThe organic layer was washed with saturated aqueous sodium hydrogen carbonate
  4. dry with materialbrine, dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified on the Isco™ Companion (12 g column: 0-11% MeOH in DCM)

Quellen und Nachweise

ORD-Eintrag
ord-8797c8f9f8764bd697c5284f6f3bada2
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07906645B2

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