2-(4-Aminophenyl)-1-(4-methylpiperazin-1-yl)ethan-1-one → 4-[2-(4-Methylpiperazin-1-yl)ethyl]aniline

HRID 2117636Notes

Reaction equation

HRID 2117636 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]([CH2:10][C:11]2[CH:17]=[CH:16][C:14]([NH2:15])=[CH:13][CH:12]=2)=O)[CH2:4][CH2:3]1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:8][CH2:10][C:11]2[CH:17]=[CH:16][C:14]([NH2:15])=[CH:13][CH:12]=2)[CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 167730792-(4-Aminophenyl)-1-(4-methylpiperazin-1-yl)ethan-1-oneHCID 21226445Aluminium lithium hydride

Product 1

HCID 242554804-[2-(4-Methylpiperazin-1-yl)ethyl]aniline

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-(4-Methylpiperazin-1-yl)carbonylmethylaniline (596 mg, 2.55 mmol) was treated in anhydrous THF (20 mL) under nitrogen with lithium aluminium hydride (291 mg, 2.67 mmol) overnight. The reaction was quenched with water (3×0.29 mL), 15% sodium hydroxide (3×0.29 mL) and again water (3×0.29 mL). The resulting precipitate was removed by filtration. Evaporation of the filtrate afforded the title compound as an orange oil. LC:2.5 min; Rt 0.21(m/z 220, M+H+) 90%, 1HNMR: (400MHz, CDCl3); 2.30 (3H, s), 2.40-2.73 (2H +8H, m), 2.69 (2H, m); 6.62 (2H, d, J 8.31), 6.99 (2H, d, J 8.31).

Workup

  1. customThe reaction was quenched with water (3×0.29 mL), 15% sodium hydroxide (3×0.29 mL) and again water (3×0.29 mL)
  2. customThe resulting precipitate was removed by filtration
  3. customEvaporation of the filtrate

Sources & evidence

ORD record
ord-52af421d9e364a80a57b7a3994285b40
Source dataset
uspto-grants-2008_10
Patent number
US07442698B2

Reaction notes

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