Water → 3-(4-(4-Methylpiperazin-1-yl)phenyl)butanamide

HRID 2176917Notes

Reaction equation

HRID 2176917 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][C:11]([CH:14]([CH3:18])[CH2:15][C:16]#[N:17])=[CH:10][CH:9]=2)[CH2:4][CH2:3]1.[OH2:19]>C(=O)(O)[O-].[Na+]>[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][C:11]([CH:14]([CH3:18])[CH2:15][C:16]([NH2:17])=[O:19])=[CH:10][CH:9]=2)[CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 962WaterHCID 673833103-(4-(4-Methylpiperazin-1-yl)phenyl)butanenitrile

Product 1

HCID 673827633-(4-(4-Methylpiperazin-1-yl)phenyl)butanamideYield 74%

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
90 °C

Procedure

A suspension of 3-(4-(4-methylpiperazin-1-yl)phenyl)butanenitrile (450 mg, 1.85 mmol) and poly phosphoric acid (4.5 g) was heated at 90° C. for 3 h. The reaction mixture was cooled to room temperature, diluted with cold water and basified with saturated sodium bicarbonate solution. The aqueous layer was extracted with DCM, washed with water and brine solution. The organic layer was dried over sodium sulfate, filtered and concentrated in vacuo to afford 360 mg (74%) of 3-(4-(4-methylpiperazin-1-yl)phenyl)butanamide as light yellow color solid.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionThe aqueous layer was extracted with DCM
  3. washwashed with water and brine solution
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5b51626475174093a2302519680d8ffa
Source dataset
uspto-grants-2015_06
Patent number
US09067888B2

Reaction notes

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