Potassium Carbonate → HCID 86729498, compound

HRID 712488Notes

Reaction equation

HRID 712488 reaction equation
[CH2:1]1[CH:10]2[CH:5]([CH2:6][CH2:7][NH:8][CH2:9]2)[CH2:4][CH2:3][N:2]1[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12].[Cl:18][CH:19](Br)[CH2:20][CH3:21].C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[Cl:18][CH2:19][CH2:20][CH2:21][N:8]1[CH2:9][CH:10]2[CH:5]([CH2:4][CH2:3][N:2]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:1]2)[CH2:6][CH2:7]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 36872Propane, bromochloro-HCID 53432622tert-Butyl octahydro-2,7-naphthyridine-2(1H)-carboxylate

Product 1

HCID 86729498HCID 86729498, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of tert-butyl octahydro-2,7-naphthyridine-2(1H)-carboxylate (320 mg, 1.33 mmol, 1 eq), chloro bromopropane (530 mg, 3.33 mmol, 2.5 eq) and K2CO3 (736 mg, 5.33 mmol, 4 eq) in acetone (25 mL) was heated to reflux overnight, then 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 afford the title compound as pale yellow oil (190 mg, 47%). The compound was characterized by the following spectroscopic data: MS (ESI, pos. ion) m/z: 317.2 (M+1).

Workup

  1. temperaturewas heated
  2. temperatureto reflux overnight
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated in vacuo
  5. customthe residue was purified by a silica gel column chromatography (20:1 (v/v) CH2Cl2/MeOH)

Sources & evidence

ORD record
ord-8b89746ba295496b8496e1f2eaa3cef5
Source dataset
uspto-grants-2015_11
Patent number
US09181277B2

Reaction notes

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