Triethylamine → tert-Butyl 4-(1-(pyridin-3-yl)ethyl)piperazine-1-carboxylate

HRID 416775

Reaktionsgleichung

Reaktionsgleichung von HRID 416775
N1C=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7]([N:9]1[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]1)[CH3:8].[N:22]1C=CC=C(C(O)C)[CH:23]=1.C(N(CC)CC)C.CS(Cl)(=O)=O.C(N1CCNCC1)(OC(C)(C)C)=O>CS(C)=O.CCOC(C)=O.CO.C(Cl)Cl>[N:22]1[CH:5]=[CH:4][CH:3]=[C:2]([CH:7]([N:9]2[CH2:10][CH2:11][N:12]([C:15]([O:17][C:18]([CH3:19])([CH3:20])[CH3:21])=[O:16])[CH2:13][CH2:14]2)[CH3:8])[CH:23]=1

Komponenten

9

Edukt 5

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 101192alpha-Methyl-3-pyridinemethanolHCID 143452tert-Butyl piperazine-1-carboxylateHCID 60137623tert-Butyl 4-(1-(pyridin-2-yl)ethyl)piperazine-1-carboxylate2×

Produkt 1

HCID 66622025tert-Butyl 4-(1-(pyridin-3-yl)ethyl)piperazine-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 679Dimethyl SulfoxideLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 21584119Ethylacetate methanolLösungsmittel

Versuchsvorschrift

This was prepared using the same procedure as for tert-butyl 4-(1-(pyridin-2-yl)ethyl)piperazine-1-carboxylate, but here using 1-(pyridin-3-yl)ethanol (J. Chem. Soc., Perkin Trans. 1, 2000, 4439-4444) (200 mg, 1.62 mmol), triethylamine (5.0 eq, 8.12 mmol, 1.13 mL), MsCl (2.0 eq, 3.25 mmol, 0.26 mL), CH2Cl2 (8 mL) at 0° C. for 30 minutes. A solution of ether-pentane (1:1, 20 mL) was added, the solid removed by filtration and the solvents removed in vacuo. The residue was then treated with N—BOC piperazine (4.0 eq, 6.50 mmol, 1.21 g) in DMSO (6 mL) at 60° C. for 18 h. Work up as described for tert-butyl 4-(1-(pyridin-2-yl)ethyl)piperazine-1-carboxylate, followed by column chromatography (EtOAc-MeOH, 95:5) gave the product (186 mg, 39% for two steps) as a colourless oil; 1H-NMR (500 MHz, CDCl3) 1.36 (d, J=6.8 Hz, 3H, CH3), 1.42 (s, 9H, C(CH3)3), 2.29-2.45 (m, 4H, piperazine N(CH2)2), 3.38 (t, J=5.0 Hz, 4H, piperazine N(CH2)2), 3.45 (q, J=6.8 Hz, 1H, CH), 7.23 (dd, br, J=7.9, 4.7 Hz, 1H, pyridine H-5), 7.64 (dt, J=7.8, 1.9 Hz, 1H, pyridine H-4), 8.47 (dd, J=4.8, 1.8 Hz, 1H, pyridine H-6), 8.52 (d, br, J=1.9 Hz, 1H, pyridine H-2);

Aufarbeitung

  1. customThis was prepared
  2. customat 0° C.
  3. customfor 30 minutes
  4. customthe solid removed by filtration
  5. customthe solvents removed in vacuo
  6. customgave the product (186 mg, 39% for two steps) as a colourless oil

Quellen und Nachweise

ORD-Eintrag
ord-eb915e51ed0f4cb4b0239007b64ae9a0
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08088761B2

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