Diisopropylethylamine → HCID 22719700, compound

HRID 1582066Notes

Reaction equation

HRID 1582066 reaction equation
Cl.[S:2]([N:6]1[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1)([CH3:5])(=[O:4])=[O:3].Cl[C:13]1[CH:22]=[CH:21][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:15][N:14]=1.C(N(CC)C(C)C)(C)C>CC(N(C)C)=O>[S:2]([N:6]1[CH2:11][CH2:10][N:9]([C:13]2[CH:22]=[CH:21][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:15][N:14]=2)[CH2:8][CH2:7]1)([CH3:5])(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 254249Methyl 6-chloropyridine-3-carboxylateHCID 162656121-Methanesulfonylpiperazine hydrochloride

Product 1

HCID 22719700HCID 22719700, compoundYield 69.1%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
120 °C

Procedure

1-Mesylpiperazine hydrochloride (4.24 g) was added to a solution of methyl 6-chloronicotinate (1.7 g) and N,N-diisopropylethylamine (6.3 ml) in dimethylacetamide (20 ml) and the mixture was heated at 120° C. for 2 hours. The mixture was allowed to cool to ambient temperature and poured onto crushed ice/water (50 ml) to precipitate a tan solid. The solid was collected by filtration and dried at 80° C. for 18 hours in a vacuum oven, to give 1-mesyl-4-(5-methoxycarbonyl-2-pyridyl)piperazine (2.05 g), mp 205-207° C.

Workup

  1. temperatureto cool to ambient temperature
  2. additionpoured
  3. customto precipitate a tan solid
  4. filtrationThe solid was collected by filtration
  5. customdried at 80° C. for 18 hours in a vacuum oven

Sources & evidence

ORD record
ord-9292286fd81f4345ba06273551227122
Source dataset
uspto-grants-2004_05
Patent number
US06734184B1

Reaction notes

Loading…