1-Aminopiperidine → 4-Chloro-N-1-piperidinylbutanamide

HRID 2235187Notes

Reaction equation

HRID 2235187 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][C:5](Cl)=[O:6].[N:8]1([NH2:14])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1.C(=O)(O)[O-].[Na+]>ClCCl>[Cl:1][CH2:2][CH2:3][CH2:4][C:5]([NH:14][N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1)=[O:6]

Participants

5

Reactant 3

HCID 166581-AminopiperidineHCID 783704-Chlorobutyryl chlorideHCID 516892Sodium Bicarbonate

Product 1

HCID 171645164-Chloro-N-1-piperidinylbutanamideYield 57%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add 4-chloro-butyryl chloride (5 mL, 43 mmol) to piperidin-1-ylamine (4.3 g, 43 mmol) in dichloromethane (100 mL) at room temp. Stir the reaction mixture at room temp for two hours. Add the reaction mixture into ice and saturated sodium bicarbonate solution. Extract the mixture with dichloromethane (100 mL). Wash the organic layer with saturated sodium bicarbonate solution (50 mL), dry with magnesium sulfate, filter and evaporate solvent under reduced pressure to obtain 5 g (57%) of the title compound as a white solid: Mass spectrum (ion spray): m/z=205.1 (M+H).

Workup

  1. extractionExtract the mixture with dichloromethane (100 mL)
  2. washWash the organic layer with saturated sodium bicarbonate solution (50 mL)
  3. dry with materialdry with magnesium sulfate
  4. filtrationfilter
  5. customevaporate solvent under reduced pressure

Sources & evidence

ORD record
ord-a7233f75117c4518a69bc3d835a91033
Source dataset
uspto-grants-2010_05
Patent number
US07713979B2

Reaction notes

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