Hydrochloric Acid → HCID 67195867, compound

HRID 2366823Notes

Reaction equation

HRID 2366823 reaction equation
[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([C:14]3[CH:19]=[CH:18][C:17]([CH2:20][N:21]4[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]4)=[CH:16][CH:15]=3)=[CH:11][CH:12]=2)[C@H:7]([NH:27]C=O)[CH2:6][C@@H:5]1[CH3:30])(=[O:3])[CH3:2].Cl>CO>[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([C:14]3[CH:19]=[CH:18][C:17]([CH2:20][N:21]4[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]4)=[CH:16][CH:15]=3)=[CH:11][CH:12]=2)[C@H:7]([NH2:27])[CH2:6][C@@H:5]1[CH3:30])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86669224HCID 86669224, compound

Product 1

HCID 67195867HCID 67195867, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of {(cis)-1-acetyl-2-methyl-6-[4-(1-piperidinylmethyl)phenyl]-1,2,3,4-tetrahydro-4-quinolinyl}formamide (for a preparation see Intermediate 30) (109 g, 0.27 mol) in MeOH (1 L) was added 6N HCl (136 mL, 0.8 mol). The resulting homogenous mixture was stirred at reflux for 2 hours and concentrated under vacuo. The residue was taken up in water (1 L) and washed with DCM (100 mL). The aqueous phase was basified with NaHCO3 and the organic materials were extracted with DCM (2×0.5 L) dried over Na2SO4 and concentrated to dryness. After heating of the residue in DCM (100 mL) and iPr2O (1 L) and filtration the title compound was obtained as a white precipitate (70 g, 70%)

Workup

  1. temperatureat reflux for 2 hours
  2. concentrationconcentrated under vacuo
  3. washwashed with DCM (100 mL)
  4. extractionthe organic materials were extracted with DCM (2×0.5 L)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated to dryness
  7. temperatureAfter heating of the residue in DCM (100 mL)
  8. filtrationiPr2O (1 L) and filtration the title compound

Sources & evidence

ORD record
ord-4a2a0cc46d3346039e955a635560e91b
Source dataset
uspto-grants-2014_04
Patent number
US08697725B2

Reaction notes

Loading…