Sulfuric Acid → HCID 58557779, compound

HRID 1969903Notes

Reaction equation

HRID 1969903 reaction equation
[CH2:1]([N:8]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH:9]1[CH2:14][CH2:13][CH:12]([C:15]([O:17]CC)=[O:16])[CH2:11][CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.OS(O)(=O)=O.[OH-].[Na+]>O>[CH2:20]([N:8]([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH:9]1[CH2:14][CH2:13][CH:12]([C:15]([OH:17])=[O:16])[CH2:11][CH2:10]1)[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 22287000Ethyl 4-[bis(phenylmethyl)amino]cyclohexanecarboxylate

Product 1

HCID 58557779HCID 58557779, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

To a 250 mL flask, ethyl 4-(dibenzylamino)cyclohexanecarboxylate (7.2 g, 20.5 mmol) and a solution of conc. H2SO4 (7.64 mL, 143 mmol) in water (80 mL) were added. The reaction mixture was stirred at about 90° C. for about 18 h, cooled to about 5° C. and the pH was adjusted to about 7 with the addition of 50% aqueous NaOH. The aqueous solution was extracted with ether (300 mL). The organic layer was dried over anhydrous Na2SO4, filtered and washed with ether. The filtrate was concd under reduced pressure to give 4-(dibenzylamino)cyclohexanecarboxylic acid (5.6 g, 85%) as a solid: LC/MS (Table 1, Method b) Rt=1.65 min; MS m/z: 324 (M+H)+.

Workup

  1. temperaturecooled to about 5° C.
  2. extractionThe aqueous solution was extracted with ether (300 mL)
  3. dry with materialThe organic layer was dried over anhydrous Na2SO4
  4. filtrationfiltered
  5. washwashed with ether

Sources & evidence

ORD record
ord-27317134e5ad481da7d4059a96192178
Source dataset
uspto-grants-2013_04
Patent number
US08426411B2

Reaction notes

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