Hydrochloric Acid → 4-Carbamoyl-4-(4-chloro-phenyl)-piperidine-1-carboxylic acid tert-butyl ester

HRID 917100Notes

Reaction equation

HRID 917100 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=2)([C:14]#[N:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-:23].[Na+].Cl>C(O)C>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][C:11]([C:14](=[O:23])[NH2:15])([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 49760270tert-Butyl 4-(4-chlorophenyl)-4-cyanopiperidine-1-carboxylate

Product 1

HCID 450739964-Carbamoyl-4-(4-chloro-phenyl)-piperidine-1-carboxylic acid tert-butyl esterYield 58%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 4-(4-chloro-phenyl)-4-cyano-piperidine-1-carboxylic acid tert-butyl ester (500 mg, 1.56 mmol) in ethanol (15 ml) was added 2 ml 10 N aqueous sodium hydroxide. The resulting solution was warmed to reflux for 2 hours, cooled to room temperature, poured into 1 N aqueous hydrochloric acid, and extracted into ethyl acetate. The organic extracts were washed with brine, dried over magnesium sulfate, and concentrated in vacuo. Recovered yellow oil was purified by silica gel chromatography, eluting with dichloromethane-methanol (9.6:0.4) to give the title compound (306 mg, 58%). MS m/z: 339 (M+1)

Workup

  1. temperatureThe resulting solution was warmed
  2. temperatureto reflux for 2 hours
  3. extractionextracted into ethyl acetate
  4. washThe organic extracts were washed with brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customRecovered yellow oil
  8. customwas purified by silica gel chromatography
  9. washeluting with dichloromethane-methanol (9.6:0.4)

Sources & evidence

ORD record
ord-37f881a59dc4407582feea92f5f7978e
Source dataset
uspto-grants-2007_09
Patent number
US07271176B2

Reaction notes

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