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

HRID 531103Notes

Reaction equation

HRID 531103 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 from 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 from methanol and ethyl acetate
  3. filtrationAfter filtration
  4. washthe crystals were washed with ethyl acetate

Sources & evidence

ORD record
ord-e45f8b3c60264f26ae54431b1553e1bb
Source dataset
uspto-grants-2016_05
Patent number
US09353108B2

Reaction notes

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