HCID 2502621, compound → 3-[4-(4-Methoxyphenyl)piperazin-1-yl]propan-1-amine

HRID 526045Notes

Reaction equation

HRID 526045 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][C:17]#[N:18])[CH2:11][CH2:10]2)=[CH:5][CH:4]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>CCOCC>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([N:9]2[CH2:10][CH2:11][N:12]([CH2:15][CH2:16][CH2:17][NH2:18])[CH2:13][CH2:14]2)=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 2502621HCID 2502621, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 21977013-[4-(4-Methoxyphenyl)piperazin-1-yl]propan-1-amineYield 84%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 3-(4-(4-methoxyphenyl)piperazin-1-yl)propanenitrile (0.8 g, 3.26 mmol) in 15 mL ether was added to the suspension of LiAlH4 (0.19 g, 4.89 mmol) in 5 mL of ether. The mixture was stirred at room temperature for 16 hours, then quenched with 2N NaOH (1 mL). The ether phase was dried over MgSO4 and evaporated to dryness to give 0.68 g (84%) white solid, which was used directly without further purification. 1H NMR (400 MHz, CDCl3) δ 6.89 (d, J=9.1 Hz, 2H), 6.82 (d, J=9.1 Hz, 2H), 3.75 (s, 3H), 3.15-3.04 (m, 4H), 2.87 (s, br. 2H), 2.76 (t, J=6.8 Hz, 2H), 2.67-2.53 (m, 4H), 2.51-2.37 (m, 2H), 1.75-1.54 (m, 2H). 13C NMR (101 MHz, CDCl3) δ 153.8, 145.7, 118.1, 114.4, 56.4, 55.5, 53.48, 50.6, 40.6, 30.1. Valenta, et al. (1990) Collect. Czech. Chem. Commun. 55:797-808.

Workup

  1. customquenched with 2N NaOH (1 mL)
  2. dry with materialThe ether phase was dried over MgSO4
  3. customevaporated to dryness

Sources & evidence

ORD record
ord-aaa8009ad48f44128614f231050d960b
Source dataset
uspto-grants-2016_05
Patent number
US09345703B2

Reaction notes

Loading…