Hydrochloric Acid → HCID 18005041, compound

HRID 1440695Notes

Reaction equation

HRID 1440695 reaction equation
Cl.[NH2:2][C:3]1[C:17]([Cl:18])=[CH:16][C:6]([C:7]([NH:9][CH:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[O:8])=[C:5]([O:19][CH3:20])[CH:4]=1.Br[CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24].C(=O)([O-])[O-].Cl>CN(C)C=O>[ClH:18].[NH2:2][C:3]1[C:17]([Cl:18])=[CH:16][C:6]([C:7]([NH:9][CH:10]2[CH2:15][CH2:14][N:13]([CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH2:12][CH2:11]2)=[O:8])=[C:5]([O:19][CH3:20])[CH:4]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7748Ethyl bromoacetateHCID 19660Carbonate IonHCID 18981809HCID 18981809, compound

Product 1

HCID 18005041HCID 18005041, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of-3.20 g of 4-amino-5-chloro-2-methoxy-N-(4-piperidinyl)benzamide hydrochloride, 1.22 ml of ethyl bromoacetate, 3.04 g of porassium carbonate, and 32 ml of N,N-dimethylformamide was stirred for 2.5 hours with heating at 60° C. The reaction mixture was concentrated under reduced pressure, and then the residue was added with water and extracted with dichloromethane. The extract was washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure to give brown oil. The result was converted to the hydrochloride by an ordinary method to afford 3.31 g of pale yellow crystals. Recrystallization from ethanol gave colorless plates, m.p. 196.5°-198.5° C.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionthe residue was added with water
  3. extractionextracted with dichloromethane
  4. washThe extract was washed with saturated aqueous sodium chloride solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customto give brown oil

Sources & evidence

ORD record
ord-aa72f40674a44859be63be9477007b86
Source dataset
uspto-grants-1996_03
Patent number
US05500422

Reaction notes

Loading…