Piperidine → HCID 51038042, compound

HRID 2040436Notes

Reaction equation

HRID 2040436 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-017b568b1ebe456181b80c25277e669e
Source dataset
uspto-grants-2013_11
Patent number
US08580842B2

Reaction notes

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