Hydrogen chloride-ethyl acetate → HCID 59526948, compound

HRID 384462Notes

Reaction equation

HRID 384462 reaction equation
C(OC(=O)N[N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][O:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH2:23][C:24]3[C:33]([CH3:34])=[C:32]([O:35][CH2:36][C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=4)[C:31]4[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=4)[N:25]=3)[CH:17]=2)[CH2:10][CH2:9]1)(C)(C)C.C(OCC)(=O)C.Cl>C(OCC)(=O)C.C(O)C>[CH2:36]([O:35][C:32]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[N:25]=[C:24]([CH2:23][O:22][C:18]2[CH:19]=[CH:20][CH:21]=[C:16]([O:15][CH2:14][CH:11]3[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]3)[CH:17]=2)[C:33]=1[CH3:34])[C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1

Participants

4

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 68510976HCID 68510976, compound

Product 1

HCID 59526948HCID 59526948, compoundYield 92.4%

Reagents, catalysts & solvents 1

HCID 21584252Ethanol ethylacetateSolvent

Procedure

To an ice-cold solution of 4-[(3-{[4-(benzyloxy)-3-methylquinolin-2-yl]methoxy}phenoxy)methyl]piperidine-1-carbamic acid tert-butyl ester (735 mg) in ethyl acetate-ethanol (3:1, 20 mL) was added a 4M hydrogen chloride-ethyl acetate solution (15 mL), and the mixture was stirred at room temperature for 1.5 hours. The reaction mixture was concentrated under reduced pressure, and then a 5% aqueous sodium hydrogen carbonate solution was added to the residue, followed by extraction with ethyl acetate (80 mL). The organic layer was washed with saturated brine and then dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: chloroform/methanol=20/1) to obtain 4-(benzyloxy)-3-methyl-2-{[3-(piperidin-4-ylmethoxy)phenoxy]methyl}quinoline (545 mg).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additiona 5% aqueous sodium hydrogen carbonate solution was added to the residue
  3. extractionfollowed by extraction with ethyl acetate (80 mL)
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (eluent: chloroform/methanol=20/1)

Sources & evidence

ORD record
ord-ad1fa4706302449e95f22de9ac5f29ad
Source dataset
uspto-grants-2013_02
Patent number
US08367702B2

Reaction notes

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