Piperidine → N-(2-Chloro-4-hydroxy-benzyl)-2,4,6-trimethyl-N-[4-(3-piperidin-1-yl-propyl)-phenyl]-benzenesulfonamide

HRID 1827577Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1827577
[Cl:1][C:2]1[CH:31]=[C:30]([OH:32])[CH:29]=[CH:28][C:3]=1[CH2:4][N:5]([C:18]1[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][CH:26]=O)=[CH:20][CH:19]=1)[S:6]([C:9]1[C:14]([CH3:15])=[CH:13][C:12]([CH3:16])=[CH:11][C:10]=1[CH3:17])(=[O:8])=[O:7].[NH:33]1[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C(=O)(O)[O-].[Na+]>C(Cl)Cl>[Cl:1][C:2]1[CH:31]=[C:30]([OH:32])[CH:29]=[CH:28][C:3]=1[CH2:4][N:5]([C:18]1[CH:19]=[CH:20][C:21]([CH2:24][CH2:25][CH2:26][N:33]2[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]2)=[CH:22][CH:23]=1)[S:6]([C:9]1[C:10]([CH3:17])=[CH:11][C:12]([CH3:16])=[CH:13][C:14]=1[CH3:15])(=[O:7])=[O:8]

Komponenten

6

Edukt 4

HCID 8082PiperidineHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 22137388N-(2-chloro-4-hydroxy-benzyl)-2,4,6-trimethyl-N-[4-(3-oxo-propyl)-phenyl]-benzenesulfonamide

Produkt 1

HCID 22137290N-(2-Chloro-4-hydroxy-benzyl)-2,4,6-trimethyl-N-[4-(3-piperidin-1-yl-propyl)-phenyl]-benzenesulfonamideAusbeute 120,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of N-(2-chloro-4-hydroxy-benzyl)-2,4,6-trimethyl-N-[4-(3-oxo-propyl)-phenyl]-benzenesulfonamide (0.040 g, 0.08 mmol) in 0.5 mL methylene chloride was added piperidine (0.009 g, 0.11 mmol) and NaB(OAc)3H (0.034 g, 0.16 mmol). The reaction mixture was stirred at room temperature for 24 hr. Saturated aqueous sodium bicarbonate was added and the aqueous solution was washed with methylene chloride. The organic layer was dried (magnesium sulfate) and concentrated. Medium pressure silica gel chromatography (10% methanol/methylene chloride) afforded 0.052 g of the title compound. MS 541.1 (M+1)+

Aufarbeitung

  1. washthe aqueous solution was washed with methylene chloride
  2. dry with materialThe organic layer was dried (magnesium sulfate)
  3. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-73c52ad6c1ca428994d933a807519ce9
Quelldatensatz
uspto-grants-2006_05
Patentnummer
US07053212B2

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