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

HRID 531091Notes

Reaction equation

HRID 531091 reaction equation
C([O:5]C([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[CH2:23][CH2:22][C:21]3[N:20]=[C:19]([CH2:24][CH2:25][CH3:26])[C:18]([C:27]([O:29][CH2:30][CH3:31])=[O:28])=[CH:17][C:16]=3[C:15]2=[O:32])[CH2:10][CH2:9]1)=O)(C)(C)C.[ClH:33].C(OC(C)C)(C)C>>[OH2:5].[ClH:33].[ClH:33].[O:32]=[C:15]1[N:14]([CH:11]2[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)[CH2:23][CH2:22][C:21]2[N:20]=[C:19]([CH2:24][CH2:25][CH3:26])[C:18]([C:27]([O:29][CH2:30][CH3:31])=[O:28])=[CH:17][C:16]1=2

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 7914Diisopropyl EtherHCID 117992199Ethyl 6-(1-(tert-butoxycarbonyl)piperidin-4-yl)-5-oxo-2-propyl-5,6,7,8-tetrahydro-1,6-naphthyridine-3-carboxylate

Product 1

HCID 131735653Ethyl 5-oxo-6-(piperidin-4-yl)-2-propyl-5,6,7,8-tetrahydro-1,6-naphthyridine-3-carboxylate dihydrochloride monohydrate

Procedure

Ethyl 6-(1-(tert-butoxycarbonyl)piperidin-4-yl)-5-oxo-2-propyl-5,6,7,8-tetrahydro-1,6-naphthyridine-3-carboxylate (14.9 g) was added to 2M hydrogen chloride (ethanol solution, 167 mL) at room temperature. The mixture was stirred for 4 hours. Diisopropyl ether (1.00 L) was added to the reaction mixture. The mixture was stirred for 30 minutes. The precipitate was collected by filtration, washed with diisopropyl ether, dried under reduced pressure to give the title compound (13.7 g).

Workup

  1. stirringThe mixture was stirred for 30 minutes
  2. filtrationThe precipitate was collected by filtration
  3. washwashed with diisopropyl ether
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-bcbcb6f777bc41a69212bbeda5a28240
Source dataset
uspto-grants-2016_05
Patent number
US09353108B2

Reaction notes

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