4-Formylbenzoic acid → 4-[(4-Cyclohexylphenylamino)methyl]benzoic acid

HRID 967633Notes

Reaction equation

HRID 967633 reaction equation
[CH:1]1([C:7]2[CH:13]=[CH:12][C:10]([NH2:11])=[CH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH:14]([C:16]1[CH:24]=[CH:23][C:19]([C:20]([OH:22])=[O:21])=[CH:18][CH:17]=1)=O.C([BH3-])#N.[Na+]>CO.C(O)(=O)C>[CH:1]1([C:7]2[CH:8]=[CH:9][C:10]([NH:11][CH2:14][C:16]3[CH:24]=[CH:23][C:19]([C:20]([OH:22])=[O:21])=[CH:18][CH:17]=3)=[CH:12][CH:13]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

6

Reactant 3

HCID 120884-Formylbenzoic acidHCID 807644-CyclohexylbenzenamineHCID 5003444Sodium cyanoborohydride

Product 1

HCID 223111294-[(4-Cyclohexylphenylamino)methyl]benzoic acidYield 78.1%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent2×

Procedure

4-Cyclohexylaniline (8.0 g, 53 mmol) was dissolved in methanol (200 mL) and a suspension of 4-formylbenzoic acid (9.4 g, 53 mmol) in glacial acetic acid (12 mL) was added in portions and the resulting mixture was heated at reflux temperature for 1.5 hour. After cooling to room temperature a mixture of sodium cyano borohydride (5.0 g, 80 mmol) in methanol (100 mL) was added in portions, and the resulting mixture was stirred at room temperature for 16 hours. The mixture was filtered and washed thoroughly with water and dried in vacuo at 50° C. for 3 days to afford 12.8 g (78%) of 4-[(4-cyclohexylphenylamino)methyl]benzoic acid.

Workup

  1. additionwas added in portions
  2. temperaturethe resulting mixture was heated
  3. temperatureat reflux temperature for 1.5 hour
  4. additionwas added in portions
  5. filtrationThe mixture was filtered
  6. washwashed thoroughly with water
  7. customdried in vacuo at 50° C. for 3 days

Sources & evidence

ORD record
ord-d4320dbdb1b747198798fbe85995c218
Source dataset
uspto-grants-2005_10
Patent number
US06953812B2

Reaction notes

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