Water → 4-(Pyrrolidin-1-ylmethyl)aniline

HRID 546614Notes

Reaction equation

HRID 546614 reaction equation
[N:1]1([C:6]([C:8]2[CH:14]=[CH:13][C:11]([NH2:12])=[CH:10][CH:9]=2)=O)[CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[N:1]1([CH2:6][C:8]2[CH:14]=[CH:13][C:11]([NH2:12])=[CH:10][CH:9]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 5778004-(Pyrrolidin-1-ylcarbonyl)anilineHCID 21226445Aluminium lithium hydride

Product 1

HCID 7768524-(Pyrrolidin-1-ylmethyl)anilineYield 92.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1.28 g of 4-(pyrrolidin-1-ylcarbonyl)aniline obtained in stage b) below in 100 mL of tetrahydrofuran are added, under argon, 1.28 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 1.28 mL of water, 1.28 mL of 15% (by weight) sodium hydroxide solution and 3.85 mL of water. The solid formed is filtered off and washed with ethyl acetate, and the filtrate is concentrated under reduced pressure to give 1.1 g of 4-(pyrrolidin-1-ylmethyl)aniline in the form of a dark yellow oil, 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-2b31dc900f59464ba45724722e5919af
Source dataset
uspto-grants-2011_05
Patent number
US07935819B2

Reaction notes

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