Butylamine → HCID 18361235, compound

HRID 383163Notes

Reaction equation

HRID 383163 reaction equation
Cl[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[CH2:12]([NH2:16])[CH2:13][CH2:14][CH3:15].C(N(C(C)C)CC)(C)C>C(#N)C.CCOC(C)=O>[CH2:12]([NH:16][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1)[CH2:13][CH2:14][CH3:15]

Participants

6

Reactant 3

HCID 8007ButylamineHCID 119282-ChloroquinolineHCID 81531Diisopropylethylamine

Product 1

HCID 18361235HCID 18361235, compoundYield 31%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-Chloroquinoline (500 mg, 3.06 mmol), butylamine (0.90 nrL, 9.16 mmol), and diisopropylethylamine (0.82 mL, 4.58 mmol) were dissolved in acetonitrile (5 mL), and solution refluxed 2 days. Reaction cooled and diluted with EtOAc. Reaction washed with water and brine. Organic layer dried with Na2SO4, filtered, and concentrated in vacuo. Residue purified by flash chromatography on silica gel eluting with 15% EtOAc/Hexanes to afford the desired product as a pale yellow oil (188 mg, 31% ). m/e (DCI) 201 (MH+)

Workup

  1. temperaturesolution refluxed 2 days
  2. customReaction
  3. temperaturecooled
  4. customReaction
  5. washwashed with water and brine
  6. dry with materialOrganic layer dried with Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customResidue purified by flash chromatography on silica gel eluting with 15% EtOAc/Hexanes

Sources & evidence

ORD record
ord-f2a41b58f73a4c36bf1291f9844a1ba4
Source dataset
uspto-grants-2001_10
Patent number
US06310095B1

Reaction notes

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