Phenyl chloroformate → HCID 10162692, compound

HRID 1597315Notes

Reaction equation

HRID 1597315 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.[NH:46]1[CH2:50][CH2:49][CH2:48][CH2:47]1>>[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]([N:46]4[CH2:50][CH2:49][CH2:48][CH2:47]4)=[O:23])[CH2:18][CH2:17]3)[CH2:11][CH2:10]2)=[O:7])=[C:4]([O:34][CH3:35])[CH:3]=1

Participants

4

Reactant 3

HCID 15891Phenyl chloroformateHCID 31268PyrrolidineHCID 69831129HCID 69831129, compound

Product 1

HCID 10162692HCID 10162692, compound

Procedure

To 4-amino-5-chloro-2-methoxy-N-[1-(1-phenoxycarbonyl-4-piperidinylmethyl)-4-piperidinyl]benzamide (1 g), which is prepared in the same manner as in Example 1 except that phenyl chloroformate is used instead of dimethylcarbamoyl chloride, is added pyrrolidine (3 ml), and the mixture is heated under reflux for 10 hours. 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 the solvent is evaporated under reduced pressure. The residue is purified by silica gel column chromatography (eluent; chloroform:methanol=40:1) to give the desired compound (790 mg) as white amorphous.

Workup

  1. temperaturethe mixture is heated
  2. temperatureunder reflux for 10 hours
  3. concentrationThe mixture is concentrated to dryness under reduced pressure
  4. additionto the residue is added chloroform
  5. washThe solution is washed with water
  6. dry with materiala saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate
  7. customthe solvent is evaporated under reduced pressure
  8. customThe residue is purified by silica gel column chromatography (eluent; chloroform:methanol=40:1)

Sources & evidence

ORD record
ord-d550f03a410e4c708899663036bb2e13
Source dataset
uspto-grants-2001_09
Patent number
US06294555B1

Reaction notes

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