Hydrochloric Acid → Itopride

HRID 703528Notes

Reaction equation

HRID 703528 reaction equation
[CH3:1][N:2]([CH3:14])[CH2:3][CH2:4][O:5][C:6]1[CH:13]=[CH:12][C:9]([CH2:10][NH2:11])=[CH:8][CH:7]=1.[CH3:15][O:16][C:17]1[CH:18]=[C:19]([CH:23]=[CH:24][C:25]=1[O:26][CH3:27])[C:20](Cl)=[O:21].COC1C=C(C=CC=1OC)C(O)=O.S(Cl)(Cl)=O.Cl>C1(C)C=CC=CC=1.O>[CH3:1][N:2]([CH3:14])[CH2:3][CH2:4][O:5][C:6]1[CH:13]=[CH:12][C:9]([CH2:10][NH:11][C:20](=[O:21])[C:19]2[CH:23]=[CH:24][C:25]([O:26][CH3:27])=[C:17]([O:16][CH3:15])[CH:18]=2)=[CH:8][CH:7]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 7121Veratric AcidHCID 24386Thionyl ChlorideHCID 77070Veratroyl chlorideHCID 88349p-(2-(Dimethylamino)ethoxy)benzylamine

Product 1

HCID 3792Itopride

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent2×

Procedure

To a cooled solution of 20.0 g of 4-[2-(dimethylamino)ethoxy]benzylamine in 60 ml of toluene was added a solution of 21.7 g of 3,4-dimethoxybenzoyl chloride (which was prepared with 19.7 g of 3,4-dimethoxybenzoic acid and 38.5 g of thionyl chloride in the usual manner) in 60 ml of toluene with stirring. The mixture was stirred at room temperature for 30 minutes. To the mixture was added 120 ml of water and 1 ml of concentrated hydrochloric acid. The aqueous layer was separated, washed with 20 ml of toluene and made alkaline with 20% sodium hydroxide solution to give a precipitate, which was washed with isopropyl ether, of 37.0 g of pale brownish crystals. Recrystallization of the crystals from ethanol and isopropyl ether gave the title compound as colorless needles, m.p. 111°-112° C.

Workup

  1. stirringThe mixture was stirred at room temperature for 30 minutes
  2. customThe aqueous layer was separated
  3. washwashed with 20 ml of toluene
  4. customto give a precipitate, which
  5. washwas washed with isopropyl ether, of 37.0 g of pale brownish crystals
  6. customRecrystallization of the crystals from ethanol and isopropyl ether

Sources & evidence

ORD record
ord-d8c76d5a41b545b6a4e593f956eb6a7c
Source dataset
uspto-grants-1991_01
Patent number
US04983633

Reaction notes

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