Potassium Carbonate → 3-{p-[3-(4-Phenylpiperidino)propionylamino]-benzoyl}-propionic acid

HRID 980202Notes

Reaction equation

HRID 980202 reaction equation
Cl[CH2:2][CH2:3][C:4]([NH:6][C:7]1[CH:19]=[CH:18][C:10]([C:11]([CH2:13][CH2:14][C:15]([OH:17])=[O:16])=[O:12])=[CH:9][CH:8]=1)=[O:5].C(=O)([O-])[O-].[K+].[K+].C1([N:32]2[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]2)C=CC=CC=1>CN(C)C=O>[C:7]1([CH:35]2[CH2:34][CH2:33][N:32]([CH2:2][CH2:3][C:4]([NH:6][C:7]3[CH:19]=[CH:18][C:10]([C:11]([CH2:13][CH2:14][C:15]([OH:17])=[O:16])=[O:12])=[CH:9][CH:8]=3)=[O:5])[CH2:37][CH2:36]2)[CH:19]=[CH:18][CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 200381-PhenylpiperidineHCID 221549983-[p-(3-Chloropropionylamino)-benzoyl]-propionic acid

Product 1

HCID 221549993-{p-[3-(4-Phenylpiperidino)propionylamino]-benzoyl}-propionic acidYield 171.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

56 g (200 millimoles) of 3-[p-(3-chloropropionylamino)-benzoyl]-propionic acid were stirred with 60.7 g (440 millimoles) of potassium carbonate and 35.5 g (220 millimoles) of phenylpiperidine in 900 ml of dimethylformamide for 8 hours at 80° C. 2 kg of ice/water were added, after which the crystals were filtered off under suction and recrystallized from dimethylformamide/water, and the product was dried at 50° C. under greatly reduced pressure. 70 g (86%) of 3-{p-[3-(4-phenylpiperidino)propionylamino]-benzoyl}-propionic acid were obtained as colorless crystals of melting point 237°-238° C.

Workup

  1. filtrationafter which the crystals were filtered off under suction
  2. customrecrystallized from dimethylformamide/water
  3. customthe product was dried at 50° C. under greatly reduced pressure

Sources & evidence

ORD record
ord-a7dbb923d855486babfb57ba51d20b87
Source dataset
uspto-grants-1987_01
Patent number
US04636504

Reaction notes

Loading…