Isobutylamine → N-(2-Methylpropyl)-3-[4-(trifluoromethyl)phenoxy]-1 azetidinecarboxamide

HRID 2081432Notes

Reaction equation

HRID 2081432 reaction equation
[CH3:1][CH:2]([CH3:5])[CH2:3][NH2:4].C(O)(=O)[C:7](O)=[O:8].[F:12][C:13]([F:26])([F:25])[C:14]1[CH:24]=[CH:23][C:17]([O:18][CH:19]2[CH2:22][NH:21][CH2:20]2)=[CH:16][CH:15]=1.C(N(CC)CC)C>C(Cl)Cl>[CH3:1][CH:2]([CH3:5])[CH2:3][NH:4][C:7]([N:21]1[CH2:20][CH:19]([O:18][C:17]2[CH:16]=[CH:15][C:14]([C:13]([F:12])([F:25])[F:26])=[CH:24][CH:23]=2)[CH2:22]1)=[O:8]

Participants

5

Reactant 3

HCID 6558IsobutylamineHCID 8471TriethylamineHCID 128125003-[4-(Trifluoromethyl)phenoxy]azetidine oxalate

Product 1

HCID 19799610N-(2-Methylpropyl)-3-[4-(trifluoromethyl)phenoxy]-1 azetidinecarboxamideYield 85.4%

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-[4-(trifluoromethyl)phenoxy]azetidine oxalate was added all at once followed in 30 min with 5 ml of triethylamine and stirring was continued for 18 hr. The reaction mixture was washed with water (2×25 ml), dried over magnesium sulfate, and concentrated in vacuo. The solid residue was recrystallized from ethanol/water, yielding 5.4 g (85.4%) of pale yellow crystals.

Workup

  1. additionadded via a syringe
  2. stirringstirring
  3. waitwas continued 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. customThe solid residue was recrystallized from ethanol/water

Sources & evidence

ORD record
ord-46b9ef6f4e8c40a7b218aefbac574edc
Source dataset
uspto-grants-1993_02
Patent number
US05183902

Reaction notes

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