Hydrochloric Acid → 1018987-99-9

HRID 1442667Notes

Reaction equation

HRID 1442667 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][C:11](=[C:14]([C:25]2[CH:30]=[CH:29][C:28]([C:31](=[O:37])[N:32]([CH2:34][CH2:35][OH:36])[CH3:33])=[CH:27][CH:26]=2)[C:15]2[CH:16]=[CH:17][CH:18]=[C:19]3[C:24]=2[N:23]=[CH:22][CH:21]=[CH:20]3)[CH2:10][CH2:9]1)=O)(C)(C)C.Cl>O1CCOCC1>[OH:36][CH2:35][CH2:34][N:32]([CH3:33])[C:31](=[O:37])[C:28]1[CH:27]=[CH:26][C:25]([C:14](=[C:11]2[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]2)[C:15]2[CH:16]=[CH:17][CH:18]=[C:19]3[C:24]=2[N:23]=[CH:22][CH:21]=[CH:20]3)=[CH:30][CH:29]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 24897464tert-butyl 4-((4-(N-(2-hydroxyethyl)-N-methylcarbamoyl)phenyl)(quinolin-8-yl)methylene)piperidine-1-carboxylate

Product 1

HCID 248976691018987-99-9Yield 100%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Compound 1B (4.7 g, 9.3 mmol) was treated with 4N HCl in dioxane (30 mL). 10 min. later, the mixture was decanted, and the solid was stirred in ether (40 mL) for 2 h. The ether was then decanted and the remaining yellow solid dried under high vacuum to yield 3.7 g 1C (100%). 1H NMR (300.132 MHz, DMSO, 90° C.) δ 8.98 (s, 1H), 8.47 (d, J=8.1 Hz, 1H), 7.96 (d, J=6.6 Hz, 1H), 7.69-7.57 (m, 3H), 7.38 (d, J=8.0 Hz, 2H), 7.29 (d, J=8.3 Hz, 2H), 3.53 (t, J=5.8 Hz, 2H), 3.36 (t, J=5.7 Hz, 2H), 3.23 (t, J=6.0 Hz, 2H), 3.07 (t, J=6.0 Hz, 2H), 2.92 (s, 3H), 2.63 (t, J=6.0 Hz, 2H), 2.15 (t, J=6.0 Hz, 2H). TOF MS ES+402.17.

Workup

  1. custom10 min. later, the mixture was decanted
  2. customThe ether was then decanted
  3. customthe remaining yellow solid dried under high vacuum

Sources & evidence

ORD record
ord-110f7573c0d64fd1ba3f5b4fd875a3cb
Source dataset
uspto-grants-2010_02
Patent number
US07659286B2

Reaction notes

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