Triethylamine → HCID 15053428, compound

HRID 1886597Notes

Reaction equation

HRID 1886597 reaction equation
[C:1]([N:8]1[CH:12]=[CH:11]N=C1)([N:3]1[CH:7]=[CH:6]N=[CH:4]1)=[O:2].[CH3:13][C:14](C)=[CH:15]CN.C(O)(=O)C(O)=O.[F:25][C:26]([F:39])([F:38])[C:27]1[CH:28]=[C:29]([CH:35]=[CH:36][CH:37]=1)[O:30]C1CNC1.C(N(CC)CC)C>O1CCCC1>[CH3:13][C:14]([CH3:15])=[CH:11][CH2:12][NH:8][C:1]([N:3]1[CH2:4][CH:6]([O:30][C:29]2[CH:35]=[CH:36][CH:37]=[C:27]([C:26]([F:25])([F:38])[F:39])[CH:28]=2)[CH2:7]1)=[O:2]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 1669212-Buten-1-amine, 3-methyl-HCID 19799580HCID 19799580, compound

Product 1

HCID 15053428HCID 15053428, compoundYield 91.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3.6 g (0.022 mole) of 1,1'-carbonyldiimidazole in 100 ml of tetrahydrofuran was cooled with a tap water bath and stirred under nitrogen while 1.6 g (0.022 mole) of 3-methyl-2-butenylamine was added with a syringe and needle. 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 72 hr. The reaction mixture was diluted with 500 ml of ice water and extracted with 6×50 ml of methylene chloride. The combined extracts were washed with water, dried over magnesium sulfate and concentrated to a solid residue on a rotary evaporator. Recrystallization from ethanol-water yielded 6 g of white crystals, m.p. 143°-144° C.

Workup

  1. additionwas added with a syringe
  2. stirringstirring
  3. waitcontinued for 72 hr
  4. extractionextracted with 6×50 ml of methylene chloride
  5. washThe combined extracts were washed with water
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated to a solid residue on a rotary evaporator
  8. customRecrystallization from ethanol-water

Sources & evidence

ORD record
ord-362d92db6f074d9abfa2975e9f61da97
Source dataset
uspto-grants-1992_09
Patent number
US05151418

Reaction notes

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