Reaction #42134

Reaction equation

4-carboxybenzaldehyde

HATU

biphenyl-2-ylcarbamic acid 1-(2-aminoethyl)piperidin-4-yl ester

DIPEA

→

title intermediate

Yield 92.2%

Biphenyl-2-ylcarbamic Acid 1-[2-(4-Formylbenzoylamino)ethyl]piperidin-4-yl Ester

Yield 92.2%

Solvents

DCM

DCM

Conditions

Workup

1. 1
   workup.STIRRINGThe resulting mixture was stirred at room temperature for 2 hours
2. 2
   Washwashed with saturated sodium bicarbonate (150 mL) and brine (150 mL)
3. 3
   DryingThe organic layer was dried over MgSO4
4. 4
   Filtrationfiltered
5. 5
   Concentrationconcentrated

Procedure

A mixture of 4-carboxybenzaldehyde (0.95 g, 6.35 mmol) and HATU (3.02 g, 7.94 mmol) in 55 mL of DCM was stirred at room temperature for 1 hour and then biphenyl-2-ylcarbamic acid 1-(2-aminoethyl)piperidin-4-yl ester (3 g, 5.29 mmol; prepared as described in Preparation 7) and DIPEA (4.6 mL, 26.45 mmol) were added. The resulting mixture was stirred at room temperature for 2 hours and then diluted with 100 mL of DCM and washed with saturated sodium bicarbonate (150 mL) and brine (150 mL). The organic layer was dried over MgSO4, filtered and concentrated to provide 2.3 g of the title intermediate (92% yield), which was suitable for use without further purification.

Source