Acrylonitrile → Piperidine-1-propylamine

HRID 2226620Notes

Reaction equation

HRID 2226620 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:7](#[N:10])[CH:8]=[CH2:9].N1(C(C)C#N)CCCCC1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C(O)C.O1CCCC1>[NH2:10][CH2:7][CH2:8][CH2:9][N:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 7855AcrylonitrileHCID 8082PiperidineHCID 129574652-(Piperidin-1-yl)propanenitrileHCID 21226445Aluminium lithium hydride

Product 1

HCID 19049Piperidine-1-propylamine

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Reaction of piperidine (Aldrich, 8.4 g, 100 mmol) with acrylonitrile (7.96 g, 150 mmol) in ethanol (25 mL), reduction of the resulting piperidinopropionitrile with lithium aluminum hydride (5 g, 125 mmol) in tetrahydrofuran (150 mL), work-up and distillation under reduced pressure as described for Example 3 gave the title compound. Yield: 3 g (21%); bp. 65°-66° (6 Torr); [lit. bp. 110°-115° C. (31 Torr), J. Corse et al., J. Amer. Chem. Soc., 68, 1911 (1946)].

Workup

  1. distillationdistillation under reduced pressure

Sources & evidence

ORD record
ord-f036c09dfb994ae8973e66bcfb8ebc39
Source dataset
uspto-grants-1994_09
Patent number
US05349063

Reaction notes

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