Methyl iodide → Batanopride

HRID 620251Notes

Reaction equation

HRID 620251 reaction equation
[H-].[Na+].[NH2:3][C:4]1[C:19]([Cl:20])=[CH:18][C:7]([C:8]([NH:10][CH2:11][CH2:12][N:13]([CH2:16][CH3:17])[CH2:14][CH3:15])=[O:9])=[C:6]([O:21][CH2:22][C:23](=[O:25])[CH3:24])[CH:5]=1.[H][H].I[CH3:29]>CN(C=O)C>[NH2:3][C:4]1[C:19]([Cl:20])=[CH:18][C:7]([C:8]([NH:10][CH2:11][CH2:12][N:13]([CH2:16][CH3:17])[CH2:14][CH3:15])=[O:9])=[C:6]([O:21][CH:22]([CH3:29])[C:23](=[O:25])[CH3:24])[CH:5]=1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 141168894-Amino-5-chloro-N-(2-diethylamino-ethyl)-2-(2-oxo-propoxy)-benzamideHCID 178418361HCID 178418361, compound

Product 1

HCID 59692Batanopride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred suspension of sodium hydride (40 mg of 60%, 1 mmole, washed with n-pentane) in DMF (2 ml) was added 4-amino-5-chloro-N-[2-(diethylamino)ethyl]-2-(2-propanon-1-yl)oxybenzamide, prepared in Example 5, (0.349 g, 1 mmole) under nitrogen. The mixture was stirred until evolution of hydrogen subsided, when iodomethane (0.07 ml, 160 mg, 1.0 mmol) was added and stirring continued for 1 hour. The mixture was partitioned between water and methylene chloride, and the organic phase washed with water, dried, concentrated and the residue chromatographed on deactivated silica using methylene chloride (100), methanol (4.5), ammonia (0.5) solvent system. The appropriate fractions were combined to give 160 mg of the title compound as a heavy oil. The NMR spectrum (90 MHz) in CDCl3 gave the following resonances: δ 8.24 (s, superimposed over broad singlet, 2H); 6.08 (s, 1H); 4.70 (q, J=5.4 Hz, 1H); 4.44 (s, 2H); 3.56 (m, 2H); 2.62 (m, 6H); 2.2 (s, 3H); 1.6 (d, J=5.4 Hz, 3H); 1.04 (t, 6H).

Workup

  1. customprepared in Example 5, (0.349 g, 1 mmole) under nitrogen
  2. customThe mixture was partitioned between water and methylene chloride
  3. washthe organic phase washed with water
  4. customdried
  5. concentrationconcentrated
  6. customthe residue chromatographed on deactivated silica

Sources & evidence

ORD record
ord-33ab082e4107423eb460a1b05b26c88b
Source dataset
uspto-grants-1989_04
Patent number
US04820715

Reaction notes

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