Hydrochloric Acid → Methyl 2-ethyl-5-oxo-6-(piperidin-4-yl)-5,6,7,8-tetrahydro-1,6-naphthyridine-3-carboxylate dihydrochloride

HRID 531114Notes

Reaction equation

HRID 531114 reaction equation
[ClH:1].C(OC([N:9]1[CH2:14][CH2:13][CH:12]([N:15]2[CH2:24][CH2:23][C:22]3[N:21]=[C:20]([CH2:25][CH3:26])[C:19]([C:27]([O:29][CH3:30])=[O:28])=[CH:18][C:17]=3[C:16]2=[O:31])[CH2:11][CH2:10]1)=O)(C)(C)C>>[ClH:1].[ClH:1].[CH2:25]([C:20]1[C:19]([C:27]([O:29][CH3:30])=[O:28])=[CH:18][C:17]2[C:16](=[O:31])[N:15]([CH:12]3[CH2:11][CH2:10][NH:9][CH2:14][CH2:13]3)[CH2:24][CH2:23][C:22]=2[N:21]=1)[CH3:26]

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 117992327Methyl 6-(1-(tert-butoxycarbonyl)piperidin-4-yl)-2-ethyl-5-oxo-5,6,7,8-tetrahydro-1,6-naphthyridine-3-carboxylate

Product 1

HCID 117992384Methyl 2-ethyl-5-oxo-6-(piperidin-4-yl)-5,6,7,8-tetrahydro-1,6-naphthyridine-3-carboxylate dihydrochloride

Procedure

A mixture of 2M hydrogen chloride (methanol solution, 236 mL) and methyl 6-(1-(tert-butoxycarbonyl)piperidin-4-yl)-2-ethyl-5-oxo-5,6,7,8-tetrahydro-1,6-naphthyridine-3-carboxylate (19.7 g) was stirred at room temperature under nitrogen atmosphere for 4 hours and concentrated in vacuo. The residue was crystallized with methanol and ethyl acetate. After filtration, the crystals were washed with ethyl acetate to give the title compound (18.5 g).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was crystallized with methanol and ethyl acetate
  3. filtrationAfter filtration
  4. washthe crystals were washed with ethyl acetate

Sources & evidence

ORD record
ord-e81c8c2b7e67429aa68581ce132f34aa
Source dataset
uspto-grants-2016_05
Patent number
US09353108B2

Reaction notes

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