Morpholine → 4-Hexyl-3-nitrobenzoic acid morpholide

HRID 1598599Notes

Reaction equation

HRID 1598599 reaction equation
[CH2:1]([C:7]1[CH:15]=[CH:14][C:10]([C:11]([OH:13])=O)=[CH:9][C:8]=1[N+:16]([O-:18])=[O:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].Cl.C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1.[NH:41]1[CH2:46][CH2:45][O:44][CH2:43][CH2:42]1>C(Cl)(Cl)Cl>[CH2:1]([C:7]1[CH:15]=[CH:14][C:10]([C:11]([N:41]2[CH2:46][CH2:45][O:44][CH2:43][CH2:42]2)=[O:13])=[CH:9][C:8]=1[N+:16]([O-:18])=[O:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

6

Reactant 4

HCID 8083MorpholineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 18929684HCID 18929684, compound

Product 1

HCID 540077734-Hexyl-3-nitrobenzoic acid morpholideYield 87.7%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

The compound ([5]-(53)-75) (7.60 g) prepared in Example 61 was dissolved in anhydrous chloroform (152 ml). Then, 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (6.37 g), 1-hydroxybenzotriazole (4.48 g), and morpholine (6.31 g) were added to the solution. The reaction mixture was stirred at room temperature for 7 hours. After the reaction was completed, chloroform was added. The solution was washed with 0.5N HCl aqueous solution, 0.5N NaOH aqueous solution, and distilled water. After the organic layer was dried over anhydrous sodium sulfate, the solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (Kieselgel 60=150 g, hexane/ethyl acetate=1/1) to obtain the above-captioned compound ([5]-(54)-75) (8.50 g) as a white solid.

Workup

  1. washThe solution was washed with 0.5N HCl aqueous solution, 0.5N NaOH aqueous solution
  2. distillationdistilled water
  3. dry with materialAfter the organic layer was dried over anhydrous sodium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (Kieselgel 60=150 g, hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-a0b06c0c44fb4c819a312a41cf9f8b24
Source dataset
uspto-grants-1998_04
Patent number
US05739131

Reaction notes

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