Hydrochloric Acid → (R)-ethyl 6-iodo-4-oxo-1-(piperidin-3-ylmethyl)-1,4-dihydroquinoline-3-carboxylate

HRID 2061879Notes

Reaction equation

HRID 2061879 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH2:11][C@@H:10]([CH2:14][N:15]2[C:24]3[C:19](=[CH:20][C:21]([I:25])=[CH:22][CH:23]=3)[C:18](=[O:26])[C:17]([C:27]([O:29][CH2:30][CH3:31])=[O:28])=[CH:16]2)[CH2:9]1)=O)(C)(C)C.Cl>ClCCl>[I:25][C:21]1[CH:20]=[C:19]2[C:24](=[CH:23][CH:22]=1)[N:15]([CH2:14][C@@H:10]1[CH2:11][CH2:12][CH2:13][NH:8][CH2:9]1)[CH:16]=[C:17]([C:27]([O:29][CH2:30][CH3:31])=[O:28])[C:18]2=[O:26]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59415740HCID 59415740, compound2×

Product 1

HCID 59415796(R)-ethyl 6-iodo-4-oxo-1-(piperidin-3-ylmethyl)-1,4-dihydroquinoline-3-carboxylateYield 104.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-ethyl 1-((1-(tert-butoxycarbonyl)piperidin-3-yl)methyl)-6-iodo-4-oxo-1,4-dihydroquinoline-3-carboxylate (Intermediate 112, 2.47 g, 4.57 mmol, 1 equiv.) in dichloromethane (18 mL) was added 4 N hydrogen chloride (4.57 mL, 18.28 mmol, 4 equiv.). This was stirred at room temperature for 12 h. The precipitate was washed with diethyl ether and dried to provide (R)-ethyl 6-iodo-4-oxo-1-(piperidin-3-ylmethyl)-1,4-dihydroquinoline-3-carboxylate as a light yellow solid (2.1 g, >99%).

Workup

  1. washThe precipitate was washed with diethyl ether
  2. customdried

Sources & evidence

ORD record
ord-001cdd2ce86446058d6dda482f5f3a3d
Source dataset
uspto-grants-2012_10
Patent number
US08283361B2

Reaction notes

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