N-(3-Aminopropyl)morpholine → HCID 2848698, compound

HRID 1442646Notes

Reaction equation

HRID 1442646 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.[N:11]1([CH2:17][CH2:18][CH2:19][NH2:20])[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1>CS(C)=O.Cl>[N:11]1([CH2:17][CH2:18][CH2:19][NH:20][C:2]2[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=2)[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1

Participants

5

Reactant 2

HCID 61055N-(3-Aminopropyl)morpholineHCID 783082-Chloro-5-nitropyridine

Product 1

HCID 2848698HCID 2848698, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
50 °C

Procedure

2-chloro-5-nitro-pyridine Compound 16a1 (6.06 g, 38.2 mmol) and 3-morpholin-4-yl-propylamine Compound 9a (6.27 mL, 42.1 mmol) were combined in DMSO (100 mL) and heated to 50° C. After 2.5 hours the reaction mixture was diluted with 0.5 M HCl and washed with ethyl ether. The aqueous layer was adjusted to pH 11 with NaOH and extracted with EtOAc. The combined organic layers were dried over MgSO4 and concentrated to provide (3-morpholin-4-yl-propyl)-(5-nitro-pyridin-2-yl)-amine Compound 19a1. Using the procedure of Example 1, Compound 19a1 was used in place of Compound 1n3 with AcOH (30 mL) replacing EtOAc as solvent. 10% Pd/C (3.1 g) was added to the solution and the reaction was carried forward to provide N2-(3-morpholin-4-yl-propyl)-pyridine-2,5-diamine Compound 19a. 1H NMR (CDCl3) δ 7.67 (d, J=3.0 Hz, 1H); 6.95 (dd, J=8.6, 3.0 Hz, 1H); 6.31(d, J=8.6 Hz, 1H); 3.77-3.66 (m, 4H); 2.52-2.38 (m, 8H); 2.08.(p, J=6.8Hz, 2H). MS 267 (MH+).

Workup

  1. washwashed with ethyl ether
  2. extractionextracted with EtOAc
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-3d5bdc28b0e1488ab9e56f2c0c954d75
Source dataset
uspto-grants-2010_02
Patent number
US07659284B2

Reaction notes

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