Hydrochloric Acid → 4-(Azetidin-3-yl)morpholine

HRID 2091868Notes

Reaction equation

HRID 2091868 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([CH:7]2[CH2:10][N:9](C(OC(C)(C)C)=O)[CH2:8]2)[CH2:3][CH2:2]1.Cl.O1CCOCC1>C(Cl)Cl>[NH:9]1[CH2:10][CH:7]([N:4]2[CH2:5][CH2:6][O:1][CH2:2][CH2:3]2)[CH2:8]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 673432951-Azetidinecarboxylic acid, 3-(4-morpholinyl)-, 1,1-dimethylethyl ester

Product 1

HCID 134019734-(Azetidin-3-yl)morpholine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-butyl 3-morpholinoazetidine-1-carboxylate (31 mg) was treated with 4N HCl in dioxane (5 eq) in 1 mL of DCM. The reaction mixture was stirred for 3 hours at room temperature and then concentrated to dryness to yield 4-(azetidin-3-yl)morpholine in quantitative yield. 4-(6-(Bromomethyl)-2-chloropyrido[3,2-d]pyrimidin-4-yl)morpholine 7 (0.413 g) was reacted with 4-(azetidin-3-yl)morpholine via General Procedure B to afford 0.4 g 4-(1-((2-chloro-4-morpholinopyrido[3,2-d]pyrimidin-6-yl)methyl)azetidin-3-yl)morpholine

Workup

  1. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-f2f51504fc6d4b659209602847de7061
Source dataset
uspto-grants-2013_05
Patent number
US08440651B2

Reaction notes

Loading…