Benzoyl chloride → HCID 20145253, compound

HRID 648641Notes

Reaction equation

HRID 648641 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:10][C:11]1[CH:12]=[CH:13][C:14]([N:32]2[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]2)=[C:15]([CH:17]([CH:19]([C:29]([NH2:31])=[O:30])[C:20]2[CH:28]=[CH:27][C:23]([C:24]([OH:26])=[O:25])=[CH:22][CH:21]=2)[CH3:18])[CH:16]=1.C(N(CC)CC)C>CN(C)C=O>[C:1]([NH:10][C:11]1[CH:12]=[CH:13][C:14]([N:32]2[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]2)=[C:15]([CH:17]([CH:19]([C:29]([NH2:31])=[O:30])[C:20]2[CH:28]=[CH:27][C:23]([C:24]([OH:26])=[O:25])=[CH:22][CH:21]=2)[CH3:18])[CH:16]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 20145241HCID 20145241, compound

Product 1

HCID 20145253HCID 20145253, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

An amount of 0.30 ml (2.62 m mol) of benzoyl chloride was added dropwise to a solution of 1 gm (2.62 m mol) of 4-[(1-(5-amino-2-piperidino-phenyl)-ethyl)-aminocarbonylmethyl]-benzoic acid and of 0.37 ml (2.62 m mol) of triethylamine in 10 ml of anhydrous dimethyl formamide. After stirring for two hours at 20° to 30° C., the reaction mixture was evaporated in vacuo and distributed between water and ethyl acetate. The organic phase was dried, filtered, and evaporated in vacuo. The evaporation residue (1.12 gm) was recrystallized from ethanol by addition of activated charcoal.

Workup

  1. customthe reaction mixture was evaporated in vacuo
  2. customThe organic phase was dried
  3. filtrationfiltered
  4. customevaporated in vacuo
  5. customThe evaporation residue (1.12 gm) was recrystallized from ethanol by addition of activated charcoal

Sources & evidence

ORD record
ord-17f02ebd966d463e845530d2aa1aef43
Source dataset
uspto-grants-1988_04
Patent number
US04735959

Reaction notes

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