Diisopropylethylamine → 3,4-Dichlorophenyl 4-[(1-methylpiperidin-3-yl)methyl]piperazine-1-carboxylate

HRID 2371134Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2371134
Cl[C:2]([O:4][C:5]1[CH:10]=[CH:9][C:8]([Cl:11])=[C:7]([Cl:12])[CH:6]=1)=[O:3].[CH3:13][N:14]1[CH2:19][CH2:18][CH2:17][CH:16]([CH2:20][N:21]2[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]2)[CH2:15]1.C(N(CC)C(C)C)(C)C.C(=O)(O)[O-].[Na+]>ClCCl>[CH3:13][N:14]1[CH2:19][CH2:18][CH2:17][CH:16]([CH2:20][N:21]2[CH2:26][CH2:25][N:24]([C:2]([O:4][C:5]3[CH:10]=[CH:9][C:8]([Cl:11])=[C:7]([Cl:12])[CH:6]=3)=[O:3])[CH2:23][CH2:22]2)[CH2:15]1

Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 27369401-[(1-Methylpiperidin-3-yl)methyl]piperazineHCID 1307789072305-24-9

Produkt 1

HCID 576567323,4-Dichlorophenyl 4-[(1-methylpiperidin-3-yl)methyl]piperazine-1-carboxylateAusbeute 60,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

3,4-Dichlorophenyl chloroformate (282 mg) in dichloromethane (10 ml) was added to a solution of 1-[(1-methylpiperidin-3-yl)methyl]piperazine (246 mg) in dichloromethane (2 ml) at room temperature. N,N-Diisopropylethylamine (0.44 ml) was added and the mixture stirred for 18 hours. Saturated aqueous sodium bicarbonate solution (5 ml) was added and the dichloromethane layer separated then concentrated in vacuo onto silica gel (0.5 g). The resulting powder was subjected to chromatography on silica gel (20 g) using a gradient of 100% dichloromethane through to 20% methanolic ammonia in dichloromethane to give the title compound (292 mg).

Aufarbeitung

  1. customthe dichloromethane layer separated
  2. concentrationthen concentrated in vacuo onto silica gel (0.5 g)

Quellen und Nachweise

ORD-Eintrag
ord-65f958bc4af24553b7b772b49832bf1f
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08710224B2

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