Tetrahydrofuran → 4-(4-Dimethylaminomethyl-2-pyridyl)butylamine

HRID 851489

Reaction equation

HRID 851489 reaction equation
[C:1]([CH2:3][CH2:4][CH2:5][C:6]1[CH:11]=[C:10]([CH2:12][N:13]([CH3:15])[CH3:14])[CH:9]=[CH:8][N:7]=1)#[N:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].O1CCCC1.[OH-].[Na+]>C(OCC)C.O>[CH3:14][N:13]([CH2:12][C:10]1[CH:9]=[CH:8][N:7]=[C:6]([CH2:5][CH2:4][CH2:3][CH2:1][NH2:2])[CH:11]=1)[CH3:15]

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 132926072-(3-Cyanopropyl)-4-dimethylaminomethylpyridineHCID 21226445Aluminium lithium hydride

Product 1

HCID 202390724-(4-Dimethylaminomethyl-2-pyridyl)butylamineYield 100%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×

Procedure

2-(3-Cyanopropyl)-4-dimethylaminomethylpyridine (1 g) in diethyl ether (15 ml) was added dropwise to a rapidly stirred suspension of lithium aluminium hydride (0.76 g) in ether (45 ml). The solution was stirred for 2.5 hours. Wet tetrahydrofuran, followed by 16% sodium hydroxide (1 ml) and then water was added and the mixture was filtered. The filtrate was evaporated to give 4-(4-dimethylaminomethyl-2-pyridyl)butylamine (1.02 g) as a clear oil.

Workup

  1. filtrationthe mixture was filtered
  2. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-3abd27ae7a80439e923870d24cef74ba
Source dataset
uspto-grants-1983_05
Patent number
US04385058

Linked notes

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