Water → HCID 54011963, compound

HRID 1268030Notes

Reaction equation

HRID 1268030 reaction equation
[C:1]([O:5][C:6](=[O:16])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([NH2:14])=[C:10]([Cl:15])[CH:9]=1)([CH3:4])([CH3:3])[CH3:2].[N:17]1([CH2:23][CH2:24][OH:25])[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1.[O:26]1CCC[CH2:27]1.O>ClCCl>[N:17]1([CH2:23][CH2:24][O:25][C:27](=[O:26])[NH:14][C:11]2[CH:12]=[CH:13][C:8]([NH:7][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:16])=[CH:9][C:10]=2[Cl:15])[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1

Participants

6

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 18232N-PiperidinoethanolHCID 53871184HCID 53871184, compound

Product 1

HCID 54011963HCID 54011963, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of 1,1-carbonyl-di-(1,2,4)-triazole (4.0 g) in dichloromethane (40 mL) is added a solution of (4-amino-3-chloro-phenyl)carbamic acid tert-butyl ester (5.0 g) in dichloromethane (45 mL) dropwise over 20 minutes. The reaction is stirred at room temperature for 30 minutes at which point a precipitate forms. To this mixture is added piperidineethanol (6.6 mL) and tetra-hydrofuran (20 mL) is added to maintain homogeneity. After heating at reflux overnight the reaction is cooled and then poured into water, the organic layer separated and then washed with saturated aqueous sodium chloride. The solution is dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to a crude oil that is purified by chromatography over silica gel (5% methanol in dichloromethane is used as the eluant) to give the desired product as a white foam.

Workup

  1. additionis added
  2. temperatureto maintain homogeneity
  3. temperatureAfter heating
  4. temperatureat reflux overnight the reaction
  5. temperatureis cooled
  6. customthe organic layer separated
  7. washwashed with saturated aqueous sodium chloride
  8. dry with materialThe solution is dried over anhydrous sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure to a crude oil that
  11. customis purified by chromatography over silica gel (5% methanol in dichloromethane

Sources & evidence

ORD record
ord-c58511f0207f477087f0f6686083f135
Source dataset
uspto-grants-2003_04
Patent number
US06555561B2

Reaction notes

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