Dimethylcarbamoyl Chloride → HCID 9955502, compound

HRID 1597312Notes

Reaction equation

HRID 1597312 reaction equation
[NH2:1][C:2]1[C:23]([Cl:24])=[CH:22][C:5]([C:6]([NH:8][CH:9]2[CH2:14][CH2:13][N:12]([CH2:15][CH:16]3[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]3)[CH2:11][CH2:10]2)=[O:7])=[C:4]([O:25][CH3:26])[CH:3]=1.C(N(CC)CC)C.[CH3:34][N:35]([CH3:39])[C:36](Cl)=[O:37]>C(Cl)Cl>[NH2:1][C:2]1[C:23]([Cl:24])=[CH:22][C:5]([C:6]([NH:8][CH:9]2[CH2:14][CH2:13][N:12]([CH2:15][CH:16]3[CH2:17][CH2:18][N:19]([C:36](=[O:37])[N:35]([CH3:39])[CH3:34])[CH2:20][CH2:21]3)[CH2:11][CH2:10]2)=[O:7])=[C:4]([O:25][CH3:26])[CH:3]=1

Participants

5

Reactant 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 8471TriethylamineHCID 10937790HCID 10937790, compound

Product 1

HCID 9955502HCID 9955502, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-amino-5-chloro-2-methoxy-N-[1-(4-piperidinylmethyl)-4-piperidinyl]benzamide (610 mg) in methylene chloride (30 ml) is added triethylamine (0.22 ml), and further thereto is added dimethylcarbamoyl chloride (0.15 ml) under ice-cooling. The mixture is stirred at room temperature for 5 hours. The reaction mixture is washed with water and a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and the solvent is evaporated under reduced pressure. The residue is purified by basic silica gel column chromatography (eluent; chloroform) to give the desired compound (720 mg) as white amorphous.

Workup

  1. temperaturecooling
  2. washThe reaction mixture is washed with water
  3. dry with materiala saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate
  4. customthe solvent is evaporated under reduced pressure
  5. customThe residue is purified by basic silica gel column chromatography (eluent; chloroform)

Sources & evidence

ORD record
ord-126d5eba04cd49c5a5c3ae5f85ae2000
Source dataset
uspto-grants-2001_09
Patent number
US06294555B1

Reaction notes

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