Triethylamine → HCID 22054273, compound

HRID 1830381Notes

Reaction equation

HRID 1830381 reaction equation
[CH:1]1([NH2:4])[CH2:3][CH2:2]1.C(N(CC)CC)C.[Cl-].ClC1N(C)CC[NH+]1C.[CH3:21][O:22][C:23]1[C:24](=[O:51])[C:25]([CH3:50])=[C:26]([CH2:32][C:33]2[CH:34]=[CH:35][C:36]([O:42][CH2:43][C:44]3[CH:45]=[N:46][CH:47]=[CH:48][CH:49]=3)=[C:37]([CH:41]=2)[C:38](O)=[O:39])[C:27](=[O:31])[C:28]=1[O:29][CH3:30]>C(Cl)Cl>[CH:1]1([NH:4][C:38](=[O:39])[C:37]2[CH:41]=[C:33]([CH2:32][C:26]3[C:27](=[O:31])[C:28]([O:29][CH3:30])=[C:23]([O:22][CH3:21])[C:24](=[O:51])[C:25]=3[CH3:50])[CH:34]=[CH:35][C:36]=2[O:42][CH2:43][C:44]2[CH:45]=[N:46][CH:47]=[CH:48][CH:49]=2)[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 69828CyclopropylamineHCID 109867151H-Imidazolium, 2-chloro-4,5-dihydro-1,3-dimethyl-, chlorideHCID 220541715-(5,6-Dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-(3-pyridylmethyloxy)benzoic Acid

Product 1

HCID 22054273HCID 22054273, compoundYield 13%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Cyclopropylamine (0.0857 g, 1.500 mmol), triethylamine (0.152 g, 1.500 mmol) and 2-chloro-1,3-dimethylimidazolinium chloride (0.254 g, 1.500 mmol) were added to a methylene chloride solution (100 ml) of 5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-(3-pyridylmethyloxy)benzoic acid (0.2115 g, 0.500 mmol) and the resulting solution was stirred at room temperature for 13 hours. The reaction solution was poured into ice water and then extracted with methylene chloride. The extract was washed with water and then dried, and the solvent was removed by distillation. The obtained residue was purified by preparative thin-layer chromatography (chloroform:methanol=10:1) and then recrystallized from ether to obtain the titled compound (0.029 g, 0.0627 mmol, 13%).

Workup

  1. extractionextracted with methylene chloride
  2. washThe extract was washed with water
  3. customdried
  4. customthe solvent was removed by distillation
  5. customThe obtained residue was purified by preparative thin-layer chromatography (chloroform:methanol=10:1)
  6. customrecrystallized from ether

Sources & evidence

ORD record
ord-ac839786c8694feda0184d1ee8026c87
Source dataset
uspto-grants-2006_06
Patent number
US07064124B2

Reaction notes

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