Phenethylamine → HCID 59396553, compound

HRID 2383036Notes

Reaction equation

HRID 2383036 reaction equation
[F:1][C:2]1([F:11])[CH2:7][CH2:6][CH:5]([C:8]([OH:10])=O)[CH2:4][CH2:3]1.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.[C:33]1([CH2:39][CH2:40][NH2:41])[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[F:11][C:2]1([F:1])[CH2:3][CH2:4][CH:5]([C:8]([NH:41][CH2:40][CH2:39][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[O:10])[CH2:6][CH2:7]1

Participants

7

Reactant 5

HCID 1001PhenethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 27791364,4-Difluorocyclohexanecarboxylic acid

Product 1

HCID 59396553HCID 59396553, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4,4-difluorocyclohexanecarboxylic acid (1.48 g) was dissolved in methylene chloride (20 mL), and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (1.68 g), 1-hydroxybenzotriazole (1.21 g), and (2-phenylethyl)amine (1.2 mL) were sequentially added thereto, followed by stirring at room temperature for 18 hours. Then, saturated aqueous sodium bicarbonate was added to the reaction liquid which was then extracted with chloroform. The extract was washed with water and further saturated brine, and then dried over magnesium sulfate. The solvent was evaporated and the resulting residue was purified by silica gel column chromatography (hexane-EtOAc) to obtain 4,4-difluoro-N-(2-phenylethyl)cyclohexanecarboxamide (1.96 g).

Workup

  1. extractionwas then extracted with chloroform
  2. washThe extract was washed with water and further saturated brine
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was evaporated
  5. customthe resulting residue was purified by silica gel column chromatography (hexane-EtOAc)

Sources & evidence

ORD record
ord-b8d5effbf256467c9a3e638fe8188d12
Source dataset
uspto-grants-2012_09
Patent number
US08263607B2

Reaction notes

Loading…