Zacopride → N-(1-Azabicyclo[2.2.2]oct-3-yl)-5-chloro-4-[[(dimethylamino)methylene]amino]-2-methoxybenzamide

HRID 1460147Notes

Reaction equation

HRID 1460147 reaction equation
[NH2:1][C:2]1[C:18]([Cl:19])=[CH:17][C:5]([C:6]([NH:8][CH:9]2[CH:14]3[CH2:15][CH2:16][N:11]([CH2:12][CH2:13]3)[CH2:10]2)=[O:7])=[C:4]([O:20][CH3:21])[CH:3]=1>COC(OC)N(C)C.CN(C)C=O>[N:11]12[CH2:12][CH2:13][CH:14]([CH2:15][CH2:16]1)[CH:9]([NH:8][C:6](=[O:7])[C:5]1[CH:17]=[C:18]([Cl:19])[C:2]([N:1]=[CH:10][N:11]([CH3:16])[CH3:12])=[CH:3][C:4]=1[O:20][CH3:21])[CH2:10]2

Participants

4

Reactant 1

HCID 108182Zacopride

Product 1

HCID 9929034N-(1-Azabicyclo[2.2.2]oct-3-yl)-5-chloro-4-[[(dimethylamino)methylene]amino]-2-methoxybenzamideYield 121.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 78373Dimethylformamide dimethyl acetalSolvent

Procedure

A solution of 4-amino-N-(1-azabicyclo[2.2.2]oct-3-yl)-5-chloro-2-methoxybenzamide (4.03 g, 13 mmol) in dimethylformamide dimethyl acetal (15 mL) and anhydrous dimethylformamide (5 mL) was heated to 100° C. for 4 hours, then concentrated in vacuo. The residue was dissolved in 6:1 tetrahydrofuran/methanol and filtered through a short column of alumina (eluted with 6:1 tetrahydrofuran/methanol). The filtrate was concentrated in vacuo to a purple residue, which was triturated from cold ether and recrystallized (2 crops) from acetonitrile to afford 2.88 g (61%) of fine colorless needles; mp 178.5°-179.5° C.

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in 6:1 tetrahydrofuran/methanol
  3. filtrationfiltered through a short column of alumina (eluted with 6:1 tetrahydrofuran/methanol)
  4. concentrationThe filtrate was concentrated in vacuo to a purple residue, which
  5. customwas triturated from cold ether
  6. customrecrystallized (2 crops) from acetonitrile

Sources & evidence

ORD record
ord-d5f306faf23646a9a7d387ff99fc13d2
Source dataset
uspto-grants-1991_12
Patent number
US05070095

Reaction notes

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