Sodium Acetate → 4-(4-Propyl-piperazine-1-yl)-piperidine-1-carboxylic acid-tert-butylester

HRID 552308

Reaktionsgleichung

Reaktionsgleichung von HRID 552308
C([O-])(=O)C.[Na+].Br.Br.[CH2:8]([N:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1)[CH2:9][CH3:10].[C:17]([N:24]1[CH2:29][CH2:28][C:27](=O)[CH2:26][CH2:25]1)([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18].C([BH3-])#N.[Na+]>CO>[C:20]([O:19][C:17]([N:24]1[CH2:29][CH2:28][CH:27]([N:14]2[CH2:15][CH2:16][N:11]([CH2:8][CH2:9][CH3:10])[CH2:12][CH2:13]2)[CH2:26][CH2:25]1)=[O:18])([CH3:23])([CH3:22])[CH3:21]

Komponenten

6

Edukt 4

HCID 517045Sodium AcetateHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 3085288N-Propylpiperazinium dibromideHCID 5003444Sodium cyanoborohydride

Produkt 1

HCID 671639834-(4-Propyl-piperazine-1-yl)-piperidine-1-carboxylic acid-tert-butylesterAusbeute 56 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

42 g (0.50 mol) sodium acetate were added in portions to 73 g (0.25 mol) N-propylpiperazine dihydrobromide in 1 l methanol at 40° C. Subsequently, this was cooled to 0° C. and 50 g (0.25 mol) Boc-4-piperidon and 16 g (0.25 mol) sodium cyanoborohydride, in portions, were added, one after the other. Everything was then stirred at room temperature for 16 h. The reaction mixture was concentrated in a vacuum and then distributed between ethyl acetate and 1M NaOH. The organic phase was separated, washed with 1M NaOH, H2O and conc. NaCl solution, dried and concentrated in a vacuum. The residue was chromatographically purified over silica gel (mobile phase: MeOH/CH2Cl2=1/15). 43.6 g of the product were obtained.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated in a vacuum
  2. customThe organic phase was separated
  3. washwashed with 1M NaOH, H2O and conc. NaCl solution
  4. customdried
  5. concentrationconcentrated in a vacuum
  6. customThe residue was chromatographically purified over silica gel (mobile phase: MeOH/CH2Cl2=1/15)

Quellen und Nachweise

ORD-Eintrag
ord-37a9e83a751c4ebd9bdbabc557cb2c63
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07951807B2

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