Isobutylamine → HCID 19799595, compound

HRID 2081430Notes

Reaction equation

HRID 2081430 reaction equation
[C:1]([N:8]1[CH:12]=[CH:11]N=[CH:9]1)(N1C=CN=C1)=[O:2].[CH3:13][CH:14]([CH3:17])[CH2:15][NH2:16].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>[CH3:13][CH:14]([CH3:17])[CH2:15][NH:16][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 6558IsobutylamineHCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 19799580HCID 19799580, compound

Product 1

HCID 19799595HCID 19799595, compoundYield 93.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A stirred solution of 3.6 g (0.022 mole) of 1,1'-carbonyldiimidazole in 100 ml of methylene chloride under nitrogen was treated with 1.6 g (0.022 mole) of 2-methylpropylamine (added via a syringe and needle through a septum placed in one neck of the reaction flask). After stirring for 1 hr, 6.2 g (0.02 mole) of 3-[3-(trifluoromethyl)phenoxy]azetidine oxalate was added all at once followed in 30 min with 5 ml of triethylamine and stirring continued for 18 hr. The reaction mixture was washed with water (2×25 ml), dried over magnesium sulfate and concentrated in vacuo, yielding 13 g of crude solid residue. Recrystallization from ethanol/water yielded 5.9 g of product having a pink cast. A second recrystallization from cyclohexane yielded 4.8 g of fine white crystals, m.p. 124°-125° C. Rework of the filtrates yielded 1.2 g additional beige crystals.

Workup

  1. additionadded via a syringe
  2. stirringstirring
  3. waitcontinued for 18 hr
  4. washThe reaction mixture was washed with water (2×25 ml)
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customyielding 13 g of crude solid residue
  8. customRecrystallization from ethanol/water

Sources & evidence

ORD record
ord-391787e5fae9455cb3d88378c5f52140
Source dataset
uspto-grants-1993_02
Patent number
US05183902

Reaction notes

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