Hydrochloric Acid → Octahydro-[1,4]dioxino[2,3-c]pyridine

HRID 712497Notes

Reaction equation

HRID 712497 reaction equation
[O:1]1[CH:10]2[CH:5]([CH2:6][N:7](C(OC(C)(C)C)=O)[CH2:8][CH2:9]2)[O:4][CH2:3][CH2:2]1.Cl>CO>[O:1]1[CH:10]2[CH:5]([CH2:6][NH:7][CH2:8][CH2:9]2)[O:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86729501tert-butyl hexahydro-[1,4]dioxino[2,3-c]pyridine-6(7H)-carboxylate

Product 1

HCID 69545778Octahydro-[1,4]dioxino[2,3-c]pyridine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of tert-butyl hexahydro-[1,4]dioxino[2,3-c]pyridine-6(7H)-carboxylate (800 mg, 4.47 mmol, 1 eq) in a solution of HCl in MeOH (15 mL) was stirred for 1 h at room temperature and concentrated in vacuo to give octahydro-[1,4]dioxino[2,3-c]pyridine. A mixture of the above residue, 1-bromo-3-chloropropane (2.84 g, 8.17 mmol, 4 eq) and K2CO3 (2.46 mg, 17.80 mmol, 4 eq) in acetone (60 mL) was heated to reflux overnight, cooled to room temperature and filtered. The filtrate was concentrated in vacuo and the residue was purified by a silica gel column chromatography (20:1 (v/v) CH2Cl2/MeOH) to give the title compound as pale yellow oil (500 mg, 45.00%). The compound was characterized by the following spectroscopic data: MS (ESI, pos. ion) m/z: 220.1 (M+1).

Workup

  1. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fdd403a5ae284b7880c5b0e77b1c7936
Source dataset
uspto-grants-2015_11
Patent number
US09181277B2

Reaction notes

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