Water → HCID 23152875, compound

HRID 1012280Notes

Reaction equation

HRID 1012280 reaction equation
[NH2:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=1.[C:13]1(=O)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].O>O1CCCC1.C(O)(=O)C>[CH:13]1([NH:1][C:2]2[CH:3]=[CH:4][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:11][CH:12]=2)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

7

Reactant 4

HCID 962WaterHCID 2337BenzocaineHCID 7967CyclohexanoneHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 23152875HCID 23152875, compoundYield 84.9%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 4-aminobenzoate (20.00 g, 0.120 mol) and cyclohexanone (17.80 g, 0.180 mol) in tetrahydrofuran (100 ml) and acetic acid (10 ml) was added sodium triacetoxyborohydride (38.50 g, 0.180 mol) at room temperature, and the mixture was stirred for 2 hr. Water was added to the reaction mixture and the mixture was extracted with toluene. The organic layer was successively washed with water, saturated aqueous sodium hydrogen carbonate and saturated brine and dried over anhydrous magnesium sulfate. After filtration, the solvent was evaporated under reduced pressure, and hexane was added to the obtained residue. The precipitated solid was collected by filtration and washed with hexane. The obtained solid was dried in vacuo to give ethyl 4-cyclohexylaminobenzoate (25.20 g, yield 84%).

Workup

  1. extractionthe mixture was extracted with toluene
  2. washThe organic layer was successively washed with water, saturated aqueous sodium hydrogen carbonate and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationAfter filtration
  5. customthe solvent was evaporated under reduced pressure, and hexane
  6. additionwas added to the obtained residue
  7. filtrationThe precipitated solid was collected by filtration
  8. washwashed with hexane
  9. customThe obtained solid was dried in vacuo

Sources & evidence

ORD record
ord-f9c424607d274468b1f86b2aed851286
Source dataset
uspto-grants-2011_07
Patent number
US07977331B1

Reaction notes

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