Triethylamine → HCID 57457809, compound

HRID 547307

Reaction equation

HRID 547307 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 room temperature 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 8.29 g of 1-{[(3-nitroquinolin-4-yl)amino]methyl}cyclopentanol as yellow crystals.

Workup

  1. customto stand at room temperature 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-b199ed104e6045a0836f99c80e5a206e
Source dataset
uspto-grants-2011_05
Patent number
US07939526B2

Linked notes

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