Hydrochloric Acid → HCID 178516272, compound

HRID 1370340Notes

Reaction equation

HRID 1370340 reaction equation
Br[C:2]1[CH:11]=[C:10]([CH:12]([CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)[OH:13])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.Cl.[O:39]1CCOCC1>O>[CH:14]1([CH:12]([C:10]2[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[N:3]=[C:2]([OH:39])[CH:11]=2)[OH:13])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 2724141Tetrabutylammonium FluorideHCID 18511451HCID 18511451, compound

Product 1

HCID 178516272HCID 178516272, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 2-bromo-α-cyclohexyl-4-quinolinemethanol (100 mg, 0.31 mmol) in dioxan (1 mL) was treated with 1-M HCl, stirred at room temperature for 16 h, refluxed for 24 h, cooled, diluted with water (5 mL), the resulting solid filtered and dried under vacuum to give the title compound (58 mg, 73%) as a white solid: mp>250° C.; IR νmax (Nujol)/cm−1 3451, 2956, 2924, 2854, 1649, 1546, 1437, 1103, 886 and 760; NMR δH (400 MHz, DMSO-d6) 1.07-1.29 (5H, m), 1.53-1.69 (6H, m), 4.77 (1H, t, J 4.5 Hz), 5.38 (1H, d, J 4.6 Hz), 6.50 (1H, s), 7.18 (1H, t, J 7.0 Hz), 7.34 (1H, d, J 7.6 Hz), 7.49 (1H, t, J 7.0 Hz), 7.84 (1H, d, J 7.6 Hz) and 11.64 (1H, s); M/Z 258 (M+H)+.

Workup

  1. temperaturerefluxed for 24 h
  2. temperaturecooled
  3. filtrationthe resulting solid filtered
  4. customdried under vacuum

Sources & evidence

ORD record
ord-624f224ca0054bfd865ae3e1c22b7cc6
Source dataset
uspto-grants-2003_06
Patent number
US06583156B1

Reaction notes

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