Piperidine → HCID 51038042, compound

HRID 601773Notes

Reaction equation

HRID 601773 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C1([O:13][C:14](=O)[O:15][C:16]2([C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][C:41]=3[O:46][CH3:47])[C:24]3[C:19](=[CH:20][CH:21]=[C:22]([Cl:25])[CH:23]=3)[N:18]([S:26]([C:29]3[CH:30]=[CH:31][CH:32]=[C:33]4[C:38]=3[N:37]=[CH:36][CH:35]=[CH:34]4)(=[O:28])=[O:27])[C:17]2=[O:39])C=CC=CC=1.[OH-].[Na+]>C1COCC1>[Cl:25][C:22]1[CH:23]=[C:24]2[C:19](=[CH:20][CH:21]=1)[N:18]([S:26]([C:29]1[CH:30]=[CH:31][CH:32]=[C:33]3[C:38]=1[N:37]=[CH:36][CH:35]=[CH:34]3)(=[O:28])=[O:27])[C:17](=[O:39])[C:16]2([O:15][C:14]([N:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)=[O:13])[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][C:41]=1[O:46][CH3:47]

Participants

5

Reactant 3

HCID 8082PiperidineHCID 14798Sodium HydroxideHCID 67043797HCID 67043797, compound

Product 1

HCID 51038042HCID 51038042, compoundYield 57.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Piperidine (0.132 ml, 1.33 mmol) was added to a solution of the intermediate from step A (200 mg, 0.33 mmol) in THF (10 ml), and the reaction solution was stirred overnight. 2 M sodium hydroxide solution was added to the reaction mixture, which was then extracted with dichloromethane. The organic phase was washed three times with water and concentrated under reduced pressure. Recrystallization from dichloromethane/diethyl ether resulted in 112 mg of the desired product.

Workup

  1. extractionwas then extracted with dichloromethane
  2. washThe organic phase was washed three times with water
  3. concentrationconcentrated under reduced pressure
  4. customRecrystallization from dichloromethane/diethyl ether

Sources & evidence

ORD record
ord-23445a5b8b9d400c962462c0c04bbccf
Source dataset
uspto-grants-2011_03
Patent number
US07902379B2

Reaction notes

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