Water → 3-[2-(Pyrrolidin-1-yl)ethyl]aniline

HRID 546622Notes

Reaction equation

HRID 546622 reaction equation
O=[C:2]([N:11]1[CH2:15][CH2:14][CH2:13][CH2:12]1)[CH2:3][C:4]1[CH:5]=[C:6]([CH:8]=[CH:9][CH:10]=1)[NH2:7].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[N:11]1([CH2:2][CH2:3][C:4]2[CH:5]=[C:6]([CH:8]=[CH:9][CH:10]=2)[NH2:7])[CH2:15][CH2:14][CH2:13][CH2:12]1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 286896693-(2-Oxo-2-pyrrolidin-1-ylethyl)aniline

Product 1

HCID 219550223-[2-(Pyrrolidin-1-yl)ethyl]anilineYield 41.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1.46 g of 3-(2-oxo-2-pyrrolidin-1-ylethyl)aniline obtained in stage b) below in 100 mL of tetrahydrofuran are added, under argon, 1.08 g of lithium aluminium hydride. The reaction mixture is stirred for one hour at room temperature and then cooled to 0° C. and treated successively with 1.08 mL of water, 1.08 mL of 15% (by weight) sodium hydroxide solution and 3.24 mL of water. The solid formed is filtered off and washed with ethyl acetate, and the filtrate is concentrated under reduced pressure to give 0.568 g of 3-(2-pyrrolidin-1-ylethyl)aniline, the characteristics of which are as follows:

Workup

  1. temperaturecooled to 0° C.
  2. customThe solid formed
  3. filtrationis filtered off
  4. washwashed with ethyl acetate
  5. concentrationthe filtrate is concentrated under reduced pressure

Sources & evidence

ORD record
ord-793399b7bdc7402abf2152ef6764325b
Source dataset
uspto-grants-2011_05
Patent number
US07935819B2

Reaction notes

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