Hydrochloric Acid → 1018987-99-9

HRID 1011282Notes

Reaction equation

HRID 1011282 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-de0bc1f5755b4e329acd81012b6d44c1
Source dataset
uspto-grants-2011_07
Patent number
US07977355B2

Reaction notes

Loading…