Diphenic anhydride → 2'-[[[3-(4-Phenyl-1-piperidinyl)propyl]amino]-carbonyl][1,1'-biphenyl]-2-carboxylic acid

HRID 1731132

Reaction equation

HRID 1731132 reaction equation
Cl.[C:2]1([CH:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][NH2:17])[CH2:10][CH2:9]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:18]12[C:25]3=[CH:26][CH:27]=[CH:28][CH:29]=[C:24]3[C:23](=[O:30])[O:22][C:20](=[O:21])[C:19]1=[CH:31][CH:32]=[CH:33][CH:34]=2>C1(C)C=CC=CC=1>[C:2]1([CH:8]2[CH2:9][CH2:10][N:11]([CH2:14][CH2:15][CH2:16][NH:17][C:23]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[C:18]3[C:19]([C:20]([OH:22])=[O:21])=[CH:31][CH:32]=[CH:33][CH:34]=3)=[O:30])[CH2:12][CH2:13]2)[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 72794Diphenic anhydrideHCID 1317105484-Phenyl-1-piperidinepropanamine, hydrochloride

Product 1

HCID 214951832'-[[[3-(4-Phenyl-1-piperidinyl)propyl]amino]-carbonyl][1,1'-biphenyl]-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

4-Phenyl-1-piperidinepropanamine, hydrochloride (prepared in part A) (16.33 g, 53.5 mM) and diphenic anhydride (12.0 g, 53.5 mM) are refluxed in toluene for 2 hours. The mixture is allowed to stand overnight at room temperature during which time product crystallizes out. The crystals are filtered off, washed with toluene, recrystallized from ethanol, and dried at 80° to give the title compound.

Workup

  1. customcrystallizes out
  2. filtrationThe crystals are filtered off
  3. washwashed with toluene
  4. customrecrystallized from ethanol
  5. customdried at 80°

Sources & evidence

ORD record
ord-69828a33aa7f4856889aa9212ce3fcc1
Source dataset
uspto-grants-1976_11
Patent number
US03995045

Linked notes

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