Triethylamine → HCID 57457809, compound

HRID 44693

Reaction equation

HRID 44693 reaction equation
[NH2:1][CH2:2][C:3]1([OH:8])[CH2:7][CH2:6][CH2:5][CH2:4]1.C(N(CC)CC)C.Cl[C:17]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[N:20]=[CH:19][C:18]=1[N+:27]([O-:29])=[O:28]>ClCCl.O>[N+:27]([C:18]1[CH:19]=[N:20][C:21]2[C:26]([C:17]=1[NH:1][CH2:2][C:3]1([OH:8])[CH2:7][CH2:6][CH2:5][CH2:4]1)=[CH:25][CH:24]=[CH:23][CH:22]=2)([O-:29])=[O:28]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 112758084-Chloro-3-nitroquinolineHCID 130512021-(Aminomethyl)cyclopentan-1-ol

Product 1

HCID 57457809HCID 57457809, compoundYield 65.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(aminomethyl)cyclopentanol (approximately 55.2 mmol, prepared as described above) in dichloromethane (280 mL) was added triethylamine (7.76 mL, 55.7 mmol) and 4-chloro-3-nitroquinoline (9.22 g, 44.3 mmol). The mixture was allowed to stand at rt over the weekend. A solid formed that was isolated by filtration. Two more crops of solid were isolated from the mother liquor. The yellow solid was stirred in water and filtered. The solid was washed with water multiple times and was dried under vacuum with heat to give 1-{[(3-nitroquinolin-4-yl)amino]methyl}cyclopentanol as yellow crystals (8.29 g, 52%).

Workup

  1. customto stand at rt over the weekend
  2. customA solid formed that
  3. customwas isolated by filtration
  4. customTwo more crops of solid were isolated from the mother liquor
  5. filtrationfiltered
  6. washThe solid was washed with water multiple times
  7. customwas dried under vacuum
  8. temperaturewith heat

Sources & evidence

ORD record
ord-277fc0269cae449d89f44ea711dded6a
Source dataset
uspto-grants-2013_09
Patent number
US08541438B2

Linked notes

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