1,2-Dichloroethane → HCID 86610878, compound

HRID 1984930Notes

Reaction equation

HRID 1984930 reaction equation
C(OC(=O)[NH:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][CH:10]=1)(C)(C)C.[C:17]1(C2C=CC=CC=2)[C:18]([C:23](O)=[O:24])=[CH:19][CH:20]=[CH:21][CH:22]=1.[CH2:32](Cl)[CH2:33][Cl:34].[CH:36]1[CH:41]=NC2N(O)N=N[C:38]=2[CH:37]=1>C(N(CC)CC)C>[ClH:34].[NH2:7][CH2:8][C:9]1[CH:10]=[CH:11][C:12]([NH:15][C:23]([C:18]2[CH:17]=[CH:22][C:21]([C:33]3[CH:32]=[CH:38][CH:37]=[CH:36][CH:41]=3)=[CH:20][CH:19]=2)=[O:24])=[CH:13][CH:14]=1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 70357o-Phenylbenzoic acidHCID 181649HOAtHCID 2756041tert-butyl N-[(4-aminophenyl)methyl]carbamate

Product 1

HCID 86610878HCID 86610878, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To a solution of (4-amino-benzyl)-carbamic acid tert-butyl ester (1.11 g, 5 mmol), biphenyl carboxylic acid (0.99 g, 5 mmol), EDC (1.2 g, 6.25 mmol), and HOAt (0.82 g, 6 mmol) in CH2CG2 (10 mL) was added triethylamine (pH=10) and the mixture was stirred at ambient temperature for overnight. The organic layer was washed with saturated aqueous NaHCO3, 1 M aqueous HCl, water, dried over Na2SO4, filtered, and concentrated. The residue was dissolved in 50% TFA in CH2Cl2 (10 mL) and the mixture was stirred at ambient temperature. After 30 minutes, the mixture was concentrated and diluted with 1 M HCl in Et2O (5 mL). The mixture was concentrated to give biphenyl-4-carboxylic acid (4-aminomethyl-phenyl)-amide hydrochloride (828 mg, 49%).

Workup

  1. washThe organic layer was washed with saturated aqueous NaHCO3, 1 M aqueous HCl, water
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. dissolutionThe residue was dissolved in 50% TFA in CH2Cl2 (10 mL)
  6. stirringthe mixture was stirred at ambient temperature
  7. waitAfter 30 minutes
  8. concentrationthe mixture was concentrated
  9. additiondiluted with 1 M HCl in Et2O (5 mL)
  10. concentrationThe mixture was concentrated

Sources & evidence

ORD record
ord-1dbb25d3a8634737ac80a0e143a66562
Source dataset
uspto-grants-2009_06
Patent number
US07544690B2

Reaction notes

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