Water → N-ethyl-2-(1H-pyrrol-1-yl)ethanamine

HRID 1448951Notes

Reaction equation

HRID 1448951 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[N:7]1([CH2:12][CH2:13][NH:14][C:15](=O)[CH3:16])[CH:11]=[CH:10][CH:9]=[CH:8]1.O.[OH-].[Na+]>C(OCC)C.O1CCCC1>[CH2:15]([NH:14][CH2:13][CH2:12][N:7]1[CH:11]=[CH:10][CH:9]=[CH:8]1)[CH3:16]

Participants

7

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 2767072HCID 2767072, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 296009N-ethyl-2-(1H-pyrrol-1-yl)ethanamine

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred suspension of lithium aluminum hydride (10 g) in dry diethyl ether (500 ml) is added dropwise a solution of N-[2-(1H-pyrrol-1-yl)ethyl]acetamide (10 g, described in Example 1) in dry tetrahydrofuran (250 ml). The mixture is refluxed for 3 hr, stirred overnight at room temperature, and decomposed with 10 ml of water, 10 ml of 15% sodium hydroxide, and 30 ml of water. The resultant slurry is stirred for 90 min and filtered. The filtrate is dried over magnesium chloride and evaporated to give the title compound as an oil: bp 70° C./8 mm Hg and nmr(CDCl3) δ 1.06(t), 1.64(s), 2.65(q), 2.95(t), 4.03(t), 6.19(t) and 6.70(t).

Workup

  1. temperatureThe mixture is refluxed for 3 hr
  2. stirringThe resultant slurry is stirred for 90 min
  3. filtrationfiltered
  4. dry with materialThe filtrate is dried over magnesium chloride
  5. customevaporated

Sources & evidence

ORD record
ord-695e82559d19437ba965f682ece4de99
Source dataset
uspto-grants-1980_02
Patent number
US04188389

Reaction notes

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