Cyclohexylamine → HCID 86700533, compound

HRID 625192Notes

Reaction equation

HRID 625192 reaction equation
[Br:1][C:2]([F:18])([F:17])[C:3]([CH:6]1[CH2:10][CH:9]([C:11]([OH:13])=O)[CH2:8][CH:7]1[C:14]([OH:16])=O)([F:5])[F:4].[CH:19]1([NH2:25])[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1>C1(C)C=CC=CC=1>[Br:1][C:2]([F:18])([F:17])[C:3]([CH:6]1[CH2:10][CH:9]([C:11]([NH:25][CH:19]2[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)=[O:13])[CH2:8][CH:7]1[C:14]([NH:25][CH:19]1[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1)=[O:16])([F:4])[F:5]

Participants

4

Reactant 2

HCID 7965CyclohexylamineHCID 86700532HCID 86700532, compound

Product 1

HCID 86700533HCID 86700533, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Into a glass flask were charged 3.00 g (8.90 mmol) of 4-(2-bromo-1,1,2,2-tetrafluoroethyl)cyclopentane-1,3-dicarboxylic acid, 8.83 g (89.0 mmol) of cyclohexylamine and 50 g of toluene, and the mixture was refluxed using a Dean and Stark apparatus for 10 hrs. Thereafter, the solvent was distilled off, and 100 mL of dichloromethane was added thereto. The organic layer washed with 50 mL of 1 M aqueous hydrochloric acid four times, with 50 mL of an aqueous sodium bicarbonate solution three times, and then with 50 mL of saturated brine once. After washing, the solvent of the organic layer was distilled off, and purification was carried out on column chromatography to obtain 3.38 g of 4-(2-bromo-1,1,2,2-tetrafluoroethyl)-N1,N3-dicyclohexylcyclopentane-1,3-dicarboxamide (precursor compound (a-8)) represented by the following formula (a-8) (yield: 76%).

Workup

  1. temperaturethe mixture was refluxed
  2. customfor 10 hrs
  3. distillationThereafter, the solvent was distilled off
  4. addition100 mL of dichloromethane was added
  5. washThe organic layer washed with 50 mL of 1 M aqueous hydrochloric acid four times, with 50 mL of an aqueous sodium bicarbonate solution three times
  6. washAfter washing
  7. distillationthe solvent of the organic layer was distilled off
  8. custompurification

Sources & evidence

ORD record
ord-52839fd4d3784066886aadf2cd123ad2
Source dataset
uspto-grants-2016_04
Patent number
US09304393B2

Reaction notes

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