Acetic Anhydride → HCID 59527620, compound

HRID 384440Notes

Reaction equation

HRID 384440 reaction equation
[CH2:1]([O:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:12]=[C:11]([CH2:19][NH:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[C:10]=1[CH3:28])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:29](OC(=O)C)(=[O:31])[CH3:30]>N1C=CC=CC=1>[CH2:1]([O:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:12]=[C:11]([CH2:19][N:20]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[C:29](=[O:31])[CH3:30])[C:10]=1[CH3:28])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 59526889HCID 59526889, compound

Product 1

HCID 59527620HCID 59527620, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of N-{[4-(benzyloxy)-3-methylquinolin-2-yl]methyl}heptane-1-amine (153 mg) in pyridine (5 mL) was added acetic anhydride (0.06 mL), followed by stirring at room temperature for 24 hours. The reaction mixture was concentrated under reduced pressure, and water (10 mL) and 1M hydrochloric acid (10 mL) were added to the residue, followed by extraction with ethyl acetate (50 mL). The organic layer was washed sequentially with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: chloroform/methanol=20/1) to obtain N-{[4-(benzyloxy)-3-methylquinolin-2-yl]methyl}-N-heptylacetamide (158 mg).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, and water (10 mL) and 1M hydrochloric acid (10 mL)
  2. additionwere added to the residue
  3. extractionfollowed by extraction with ethyl acetate (50 mL)
  4. washThe organic layer was washed sequentially with water and 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-4820c46ab57a438181ee68a5d9d0aa41
Source dataset
uspto-grants-2013_02
Patent number
US08367702B2

Reaction notes

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