Pyridine → HCID 732341, compound

HRID 1434720Notes

Reaction equation

HRID 1434720 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10](Cl)(=[O:12])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].[N:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.Cl[CH2:21]Cl>Cl>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([N:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:21]2)(=[O:12])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6344DichloromethaneHCID 74044-Nitrobenzenesulfonyl chloride

Product 1

HCID 732341HCID 732341, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 4-nitrobenzenesulfonyl chloride (1.78 g, 8.0 mmol), pyridine (0.78 mL, 9.6 mmol), and hexamethyleneimine (0.796 g, 8.02 mmol) in dichloromethane (22 mL) was stirred for 5 hrs at 0° C., diluted with 1N HCl, and extracted with dichloromethane. The organic layer was dried (Na2SO4), filtered, concentrated, and triturated with diethyl ether to give 1-(4-nitro-benzenesulfonyl)-azepane as a brown solid. The solid was added to a mixture of HCO2NH4 (1.91 g, 30.3 mmol) and 10% Pd/C (catalytic amount) in methanol (20 mL) and ethyl acetate (4 mL), stirred overnight at about 25° C., filtered, concentrated, diluted with water, and extracted with dichloromethane. The isolated organic layer was dried (Na2SO4), filtered and concentrated to give the title compound. 1H NMR (300 MHz, CDCl3) δ 8.35 (d, 2H), 7.97 (d, 2H), 3.31 (t, 4H), 1.70-1.79 (m, 4H), 1.56-1.63 (m, 4H).

Workup

  1. extractionextracted with dichloromethane
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customtriturated with diethyl ether

Sources & evidence

ORD record
ord-aa0d32c8a64449b9a7da4e357a95face
Source dataset
uspto-grants-2009_11
Patent number
US07615570B2

Reaction notes

Loading…