Triethylamine → HCID 15053465, compound

HRID 2081399Notes

Reaction equation

HRID 2081399 reaction equation
[C:1]([N:8]1[CH:12]=[CH:11]N=[CH:9]1)(N1C=CN=C1)=[O:2].[CH2:13]([NH2:17])[C:14](=[CH2:16])[CH3:15].C(O)(=O)C(O)=O.[F:24][C:25]([F:38])([F:37])[C:26]1[CH:27]=[C:28]([CH:34]=[CH:35][CH:36]=1)[O:29]C1CNC1.C(N(CC)CC)C>C(Cl)Cl>[CH3:16][C:14](=[CH2:15])[CH2:13][NH:17][C:1]([N:8]1[CH2:9][CH:11]([O:29][C:28]2[CH:34]=[CH:35][CH:36]=[C:26]([C:25]([F:24])([F:37])[F:38])[CH:27]=2)[CH2:12]1)=[O:2]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 761412-MethylallylamineHCID 19799580HCID 19799580, compound

Product 1

HCID 15053465HCID 15053465, compoundYield 106.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3.6 g (0.022 mole) of 1,1'-carbonyldiimidazole in 75 ml of methylene chloride was stirred under nitrogen while 1.6 g (0.022 mole) of methallylamine was added with a syringe and needle through a septum installed in one neck of the reaction flask. The reaction was slightly exothermic. The reaction mixture was stirred for 1 hr, then treated with 6.2 g (0.02 mole) of 3-[3-(trifluoromethyl)phenoxy]azetidine oxalate followed in 0.5 hr with 5 ml of triethylamine and stirring continued for 16 hr. The reaction mixture was washed with 2×30 ml of water, dried over magnesium sulfate, and concentrated on a rotary evaporator to yield 6.7 g of oily residue which solidified. The residue was recrystallized from isopropyl ether to yield 5.4 g (85.9%) of fine white crystals, m.p. 90°-91° C.

Workup

  1. additionwas added with a syringe
  2. stirringstirring
  3. waitcontinued for 16 hr
  4. washThe reaction mixture was washed with 2×30 ml of water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated on a rotary evaporator

Sources & evidence

ORD record
ord-8eea33dec9eb47d1b3d817cea41f64dc
Source dataset
uspto-grants-1993_02
Patent number
US05183902

Reaction notes

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