Butylamine → HCID 19887353, compound

HRID 654454Notes

Reaction equation

HRID 654454 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=2)=[CH:9][CH2:10][CH2:11][N:12]2[CH2:23][CH2:22][C:15]3([O:19][C:18](=O)[O:17][C:16]3=[CH2:21])[CH2:14][CH2:13]2)=[CH:4][CH:3]=1.[CH2:31]([NH2:35])[CH2:32][CH2:33][CH3:34].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[OH-].[Na+]>C1(C)C(C)=CC=CC=1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=2)=[CH:9][CH2:10][CH2:11][N:12]2[CH2:13][CH2:14][C:15]3([O:19][C:18](=[O:17])[N:35]([CH2:31][CH2:32][CH2:33][CH3:34])[C:16]3=[CH2:21])[CH2:22][CH2:23]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 8007ButylamineHCID 14798Sodium HydroxideHCID 521998p-Toluenesulfonic acid monohydrateHCID 19887352HCID 19887352, compound

Product 1

HCID 19887353HCID 19887353, compoundYield 72.5%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent2×

Procedure

A mixture containing 8.2 g of 8-[4,4-bis(4-fluorophenyl)-3-butenyl]-4-methylene-2-oxo-1,3-dioxa-8-azaspiro[4,5]decane, 25 ml of xylene and 2.0 ml of butylamine is stirred at room temperature for 18 hours, then 0.8 g of p-toluenesulfonic acid monohydrate and 70 ml of xylene are added and the reaction mixture is boiled while azeotropically distilling off the water formed in the reaction. After termination of the reaction which is observed by thin layer chromatography (TLC), the mixture is cooled down and made alkaline to a pH of 9 to 10 by adding 5% by weight aqueous sodium hydroxide solution. After washing the organic phase with water to neutral and drying over anhydrous magnesium sulfate, the solvent is distilled off under reduced pressure. The crude product obtained as evaporation residue is recrystallized from ethanol under clarifying by activated carbon to give the title product in 72.5% yield, m.p.: 92°-93° C.

Workup

  1. distillationwhile azeotropically distilling off the water
  2. customformed in the reaction
  3. customAfter termination of the reaction which
  4. temperaturethe mixture is cooled down
  5. washAfter washing the organic phase with water to neutral and
  6. dry with materialdrying over anhydrous magnesium sulfate
  7. distillationthe solvent is distilled off under reduced pressure
  8. customThe crude product obtained as evaporation residue
  9. customis recrystallized from ethanol under clarifying by activated carbon

Sources & evidence

ORD record
ord-504cb59ce9384ad4bcb91395ce59a59d
Source dataset
uspto-grants-1992_07
Patent number
US05132303

Reaction notes

Loading…