Methylamine → HCID 20689431, compound

HRID 1597316Notes

Reaction equation

HRID 1597316 reaction equation
[NH2:1][C:2]1[C:32]([Cl:33])=[CH:31][C:5]([C:6]([NH:8][CH:9]2[CH2:14][CH2:13][N:12]([CH2:15][CH:16]3[CH2:21][CH2:20][N:19]([C:22](OC4C=CC=CC=4)=[O:23])[CH2:18][CH2:17]3)[CH2:11][CH2:10]2)=[O:7])=[C:4]([O:34][CH3:35])[CH:3]=1.ClC(OC1C=CC=CC=1)=O.[CH3:46][NH2:47]>C(O)C>[NH2:1][C:2]1[C:32]([Cl:33])=[CH:31][C:5]([C:6]([NH:8][CH:9]2[CH2:14][CH2:13][N:12]([CH2:15][CH:16]3[CH2:21][CH2:20][N:19]([C:22](=[O:23])[NH:47][CH3:46])[CH2:18][CH2:17]3)[CH2:11][CH2:10]2)=[O:7])=[C:4]([O:34][CH3:35])[CH:3]=1

Participants

5

Reactant 3

HCID 6329MethylamineHCID 15891Phenyl chloroformateHCID 69831129HCID 69831129, compound

Product 1

HCID 20689431HCID 20689431, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
110 °C

Procedure

To 4-amino-5-chloro-2-methoxy-N-[1-(1-phenoxycarbonyl-4-piperidinylmethyl)-4-piperidinyl]benzamide (880 mg), which is prepared in a similar manner as in Example 1 except that phenyl chloroformate is used instead of dimethylcarbamoyl chloride, is added a 30% solution of methylamine in ethanol (20 ml), and the mixture is heated at 110° C. for 8 hours in a sealed tube. The mixture is concentrated to dryness under reduced pressure, and to the residue is added chloroform. The solution is washed with water and a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue is purified by silica gel column chromatography (eluent; chloroform:methanol=20:110:1) to give the desired compound (200 mg) as amorphous.

Workup

  1. concentrationThe mixture is concentrated to dryness under reduced pressure
  2. additionto the residue is added chloroform
  3. washThe solution is washed with water
  4. dry with materiala saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue is purified by silica gel column chromatography (eluent; chloroform:methanol=20:110:1)

Sources & evidence

ORD record
ord-ae3337cd38874f5494d6af2349f218a0
Source dataset
uspto-grants-2001_09
Patent number
US06294555B1

Reaction notes

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