Acrylic Acid → 3-[4-(Biphenyl-2-ylcarbamoyloxy)piperidin-1-yl]propionic Acid

HRID 2246500Notes

Reaction equation

HRID 2246500 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([O:7][C:8](=[O:22])[NH:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:3][CH2:2]1.[C:23]([OH:27])(=[O:26])[CH:24]=[CH2:25]>ClCCl>[C:11]1([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[NH:9][C:8]([O:7][CH:4]1[CH2:3][CH2:2][N:1]([CH2:25][CH2:24][C:23]([OH:27])=[O:26])[CH2:6][CH2:5]1)=[O:22]

Participants

4

Reactant 2

HCID 6581Acrylic AcidHCID 10851461Biphenyl-2-ylcarbamic Acid Piperidin-4-yl Ester

Product 1

HCID 218806073-[4-(Biphenyl-2-ylcarbamoyloxy)piperidin-1-yl]propionic AcidYield 244.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of biphenyl-2-ylcarbamic acid piperidin-4-yl ester (50 g, 67.6 mmol) in dichloromethane (500 mL) was added acrylic acid (15.05 mL, 100 mmol). The resulting mixture was heated at 50° C. under reflux for 18 hours and then the solvent was removed. Methanol (600 mL) was added and this mixture was heated at 75° C. for 2 hours and then cooled to room temperature to form a thick slurry. The solid was collected by filtration, washed with methanol (50 mL) and air dried to afford 3-[4-(biphenyl-2-ylcarbamoyloxy)piperidin-1-yl]propionic acid (61 g, 96% purity) as white powder.

Workup

  1. temperatureunder reflux for 18 hours
  2. customthe solvent was removed
  3. additionMethanol (600 mL) was added
  4. temperaturethis mixture was heated at 75° C. for 2 hours
  5. temperaturecooled to room temperature
  6. customto form a thick slurry
  7. filtrationThe solid was collected by filtration
  8. washwashed with methanol (50 mL) and air
  9. customdried

Sources & evidence

ORD record
ord-19e8c2e81ca14597816a5efcbe1f2589
Source dataset
uspto-grants-2010_03
Patent number
US07687521B2

Reaction notes

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