Sodium Iodide → Batanopride Hydrochloride

HRID 620253Notes

Reaction equation

HRID 620253 reaction equation
Cl.[NH2:2][C:3]1[C:18]([Cl:19])=[CH:17][C:6]([C:7]([NH:9][CH2:10][CH2:11][N:12]([CH2:15][CH3:16])[CH2:13][CH3:14])=[O:8])=[C:5]([OH:20])[CH:4]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+].Cl[CH:30]([CH3:34])[C:31](=[O:33])[CH3:32]>CN(C=O)C>[ClH:19].[NH2:2][C:3]1[C:18]([Cl:19])=[CH:17][C:6]([C:7]([NH:9][CH2:10][CH2:11][N:12]([CH2:13][CH3:14])[CH2:15][CH3:16])=[O:8])=[C:5]([O:20][CH:30]([CH3:34])[C:31](=[O:33])[CH3:32])[CH:4]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 200263-Chloro-2-butanoneHCID 141168774-amino-5-chloro-N-(2-(diethylamino)ethyl)-2-hydroxybenzamide hydrochloride

Product 1

HCID 59691Batanopride HydrochlorideYield 161.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred suspension of 4-amino-5-chloro-N-[2-(diethylamino)ethyl]-2-hydroxybenzamide hydrochloride (19.4 g, 60 mmoles), potassium carbonate (41.6 g, 0.3 moles) and sodium iodide (10 g) in DMF (100 ml) was added 3-chloro-2-butanone (9.5 g, 89 mmoles) and the mixture vigorously stirred and heated to 70°-80° for 2 hours followed by cooling and partition between water and methylene chloride. The organic phase was washed with water, dried and concentrated. The residue was treated with 2N HCl and azeotroped with n-propanol, and crystallized from acetone to give 19.0 g (81%) of the title compound mp 177°-179°.

Workup

  1. temperatureheated to 70°-80° for 2 hours
  2. temperatureby cooling
  3. custompartition between water and methylene chloride
  4. washThe organic phase was washed with water
  5. customdried
  6. concentrationconcentrated
  7. additionThe residue was treated with 2N HCl
  8. customazeotroped with n-propanol
  9. customcrystallized from acetone

Sources & evidence

ORD record
ord-27be2c0b7ecf48ae9bb8a74c6fa28cd2
Source dataset
uspto-grants-1989_04
Patent number
US04820715

Reaction notes

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