Water → 2-(4-Aminobutyl)-1,3-propanediol

HRID 1587639Notes

Reaction equation

HRID 1587639 reaction equation
[C:1]([CH2:3][CH2:4][CH2:5][CH:6]([C:12](OCC)=[O:13])[C:7](OCC)=[O:8])#[N:2].[H-].[H-].[H-].[H-].[Li+].[Al+3].[H-].O>C(OCC)C>[NH2:2][CH2:1][CH2:3][CH2:4][CH2:5][CH:6]([CH2:12][OH:13])[CH2:7][OH:8]

Participants

6

Reactant 4

HCID 962WaterHCID 166653HydrideHCID 3641060Diethyl 2-(3-cyanopropyl)malonateHCID 21226445Aluminium lithium hydride

Product 1

HCID 1303832-(4-Aminobutyl)-1,3-propanediol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

6 g of diethyl 2-(3-cyanopropyl)malonate are added dropwise, at -10° C., to a suspension of 3 g of LiAlH4 in 100 ml of dry diethyl ether under N2. The mixture is slowly warmed to room temperature and then refluxed for 3 h. After renewed cooling to -10° C., the excess hydride is decomposed with water. The precipitate is removed on a frit and washed several times with diethyl ether. The ether solution is dried over MgSO4, filtered and evaporated in a rotary evaporator. Yield 0.66 g of 2-(4-aminobutyl)-1,3-propanediol, detectable in the 1H NMR and by C and H analysis. Glassy solid, melting point 126° C. (honey-like above 60° C.).

Workup

  1. temperaturerefluxed for 3 h
  2. temperatureAfter renewed cooling to -10° C.
  3. customThe precipitate is removed on a frit
  4. washwashed several times with diethyl ether
  5. dry with materialThe ether solution is dried over MgSO4
  6. filtrationfiltered
  7. customevaporated in a rotary evaporator
  8. customGlassy solid, melting point 126° C. (honey-like above 60° C.)

Sources & evidence

ORD record
ord-30faa65cfe5043e385c2cf7b832dd620
Source dataset
uspto-grants-1993_06
Patent number
US05219555

Reaction notes

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