Water → 4-(2-Pyrimidinyl)-1-piperazinebutanamine

HRID 745210Notes

Reaction equation

HRID 745210 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]([CH2:9][CH2:10][CH2:11][N:12]1[CH2:17][CH2:16][N:15]([C:18]2[N:23]=[CH:22][CH:21]=[CH:20][N:19]=2)[CH2:14][CH2:13]1)#[N:8].O.[OH-].[K+]>CCOCC>[NH2:8][CH2:7][CH2:9][CH2:10][CH2:11][N:12]1[CH2:13][CH2:14][N:15]([C:18]2[N:19]=[CH:20][CH:21]=[CH:22][N:23]=2)[CH2:16][CH2:17]1

Participants

6

Reactant 4

HCID 962Water2×HCID 14797Potassium HydroxideHCID 3986541-Piperazinebutanenitrile, 4-(2-pyrimidinyl)-HCID 21226445Aluminium lithium hydride

Product 1

HCID 128407054-(2-Pyrimidinyl)-1-piperazinebutanamine

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a cold mixture of lithium aluminum hydride (2.0 g; 5.26 mmol) and anhydrous ether (240 ml) kept at a temperature of -54° C., there was dropwise added a solution of 1-(3-cyanopropyl)-4-(2-pyrimidinyl)piperazine (8 g; 3.46 mmol) in anhydrous ether (80 ml), and the resultant mixture was kept at the same temperature as above for 1.5 hours, followed by dropwise addition of water (2 ml), a 15% aqueous potassium hydroxide solution (2 ml) and water (6 ml) in order. The reaction mixture was stirred at room temperature for 2 hours, subjected to filtration with celite and washed with chloroform. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel chromatography to give 1-(4-aminobutyl)-4-(2-pyrimidinyl)-piperazine. IR νmaxFilm (cm--1): 3100-3600, 1580, 1540.

Workup

  1. customkept at a temperature of -54° C., there
  2. customwas kept at the same temperature as above for 1.5 hours
  3. filtrationsubjected to filtration with celite
  4. washwashed with chloroform
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-cf9a51052bbd46ffb89ef7c1054e2f6a
Source dataset
uspto-grants-1986_07
Patent number
US04598078

Reaction notes

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