Tetrahydrofuran → HCID 15086598, compound

HRID 359086Notes

Reaction equation

HRID 359086 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][CH2:12][CH2:13][CH2:14][O:15][C:16]2[CH:25]=[CH:24][C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][CH:17]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH2:33](Cl)[C:34]1[CH:42]=[CH:41][C:40]2[O:39][CH2:38][O:37][C:36]=2[CH:35]=1.C1C[O:47]CC1>>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([N:11]([CH2:12][CH2:13][CH2:14][O:15][C:16]2[CH:25]=[CH:24][C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][CH:17]=2)[C:33](=[O:47])[C:34]2[CH:42]=[CH:41][C:40]3[O:39][CH2:38][O:37][C:36]=3[CH:35]=2)=[CH:9][CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 887131,3-Benzodioxole, 5-(chloromethyl)-HCID 15086590HCID 15086590, compound

Product 1

HCID 15086598HCID 15086598, compound

Procedure

Methyl 4-[3-[N-(4-tert-butylphenyl)amino]propoxy]benzoate (1.80 g) and triethylamine (3.65 ml) were dissolved in THF (40 ml), and cooled with ice, and piperonyl chloride (1.46 g) was added thereto, and the mixture was stirred at room temperature for 16 hours. After the reaction solution was concentrated under reduced pressure, water and ethyl acetate were added thereto and the mixture was separated into layers. The organic layer was washed with water 3 times, and dried under reduced water. The resulting residue was subjected to column chromatography on silica gel and eluted with chloroform to give the desired product (2.01 g).

Workup

  1. additionwas added
  2. concentrationAfter the reaction solution was concentrated under reduced pressure, water and ethyl acetate
  3. additionwere added
  4. customthe mixture was separated into layers
  5. washThe organic layer was washed with water 3 times
  6. customdried under reduced water
  7. washeluted with chloroform

Sources & evidence

ORD record
ord-676449849b93485f9b33c2a3c57a7e20
Source dataset
uspto-grants-1991_03
Patent number
US04999378

Reaction notes

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