Water → Batanopride Hydrochloride

HRID 620252Notes

Reaction equation

HRID 620252 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+].Cl[CH:28]([CH3:32])[C:29](=[O:31])[CH3:30].O>CN(C=O)C.C(Cl)Cl>[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:28]([CH3:32])[C:29](=[O:31])[CH3:30])[CH:4]=1

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 200263-Chloro-2-butanoneHCID 141168774-amino-5-chloro-N-(2-(diethylamino)ethyl)-2-hydroxybenzamide hydrochloride

Product 1

HCID 59691Batanopride HydrochlorideYield 119%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred suspension of 4-amino-5-chloro-N-[2-(diethylamino)ethyl]-2-hydroxybenzamide hydrochloride (1.94 g, 6 mmoles) and potassium carbonate (4.16 g, 30 mmoles) in DMF (10 ml) was added 3-chloro-2-butanone (0.95 g, 8.9 mmoles) and the mixture stirred for 3 hours, followed by pouring into water and extraction with methylene chloride. The extract was washed well with water, dried and concentrated in vacuo. The residue was dissolved in 1-propanol and treated with 2N HCl followed by concentration to give an oily residue. This was crystallized from acetone and the product recrystallized from 2-propanol to give 1.4 g of the title compound mp 98° C. as the hemihydrate.

Workup

  1. washThe extract was washed well with water
  2. customdried
  3. concentrationconcentrated in vacuo
  4. dissolutionThe residue was dissolved in 1-propanol
  5. additiontreated with 2N HCl
  6. concentrationfollowed by concentration
  7. customto give an oily residue
  8. customThis was crystallized from acetone
  9. customthe product recrystallized from 2-propanol

Sources & evidence

ORD record
ord-a9c2a446ca0c4b36b2f63ad7240ce226
Source dataset
uspto-grants-1989_04
Patent number
US04820715

Reaction notes

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