Triethylamine → HCID 15053371, compound

HRID 2081403Notes

Reaction equation

HRID 2081403 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].[CH2:13](N)/[CH:14]=C/C.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>[CH2:12]([NH:8][C:1]([N:3]1[CH2:4][CH:6]([O:29][C:28]2[CH:34]=[CH:35][CH:36]=[C:26]([C:25]([F:24])([F:37])[F:38])[CH:27]=2)[CH2:7]1)=[O:2])/[CH:11]=[CH:13]/[CH3:14]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 643377221035-54-1HCID 19799580HCID 19799580, compound

Product 1

HCID 15053371HCID 15053371, compoundYield 59.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3.6 g (0.022 mole) of 1,1'-carbonyldiimidazole in 60 ml of methylene chloride was cooled in an ice bath while stirring under nitrogen while 1.6 g (0.022 mole) of trans-crotylamine was added dropwise. After warming to ambient temperature, 6.2 g (0.02 mole) of 3-[3-(trifluoromethyl)phenoxy]azetidine oxalate was added all at once followed in 0.25 hr by 5 ml of triethylamine with stirring continued for 72 hr. The reaction solution was washed with 2×50 ml of water, dried over magnesium sulfate and concentrated on a rotary evaporator to a solid residue, 7 g. Recrystallization from methanol-water gave 5.5 g of slightly yellow product. A second recrystallization with charcoal treatment from isopropyl ether yielded 3.75 g (59.7%) of fine white crystals, m.p. 127°-128° C.

Workup

  1. additionwas added dropwise
  2. washThe reaction solution was washed with 2×50 ml of water
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated on a rotary evaporator to a solid residue, 7 g
  5. customRecrystallization from methanol-water
  6. customgave 5.5 g of slightly yellow product
  7. customA second recrystallization with charcoal treatment from isopropyl ether

Sources & evidence

ORD record
ord-8229158e76764c4fab11643ff8c59468
Source dataset
uspto-grants-1993_02
Patent number
US05183902

Reaction notes

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