Water → 4-(4-Phenyl-3,6-dihydropyridin-1(2H)-yl)butanenitrile

HRID 362777Notes

Reaction equation

HRID 362777 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][N:6]1[CH2:11][CH:10]=[C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:8][CH2:7]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O>C1COCC1>[C:12]1([C:9]2[CH2:10][CH2:11][N:6]([CH2:5][CH2:4][CH2:3][C:2]#[N:1])[CH2:7][CH:8]=2)[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 962WaterHCID 153385904-(4-Phenyl-3,6-dihydropyridin-1(2H)-yl)butan-1-amineHCID 21226445Aluminium lithium hydride

Product 1

HCID 214951844-(4-Phenyl-3,6-dihydropyridin-1(2H)-yl)butanenitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

N-(4-Aminobutyl)-4-phenyl-1,2,3,6-tetrahydropyridine (C) 1.8 g of lithium aluminium hydride are suspended in small portions (exothermic dissolution) in 50 ml of anhydrous THF (freshly distilled over sodium). 4.5 g of 4-(4-phenyl-1,2,3,6-tetrahydropyridinyl)butyronitrile, in solution in THF, are added dropwise at 0° C. and then reaction is allowed to take place at 0° C. for 3 hours with good stirring. The mixture is hydrolysed with a mixture of 5 ml of water in solution in 50 ml of THF and the combined mixture is allowed to stand overnight in order to agglomerate the precipitate. The precipitate is filtered on celite and the filtrate is dried over anhydrous sodium sulphate and concentrated. The residue is distilled under pump vacuum. A colourless oil is obtained. Y=86%. 1H NMR (CDCl3):1.26 (bs, 2H, --NH2), 1.43-1.66 (m, 4H, --H2C--CH2 --), 2.44-2.51 (t, 2H, --CH2 --) 2.59 (b s, 2H, --CH2 --), 2.68-2.76 (m, 4H, --CH2 --CH2 --) 3.15-3.19 (d, 2H, --CH2 --), 3.72-3.78 (q, 2H, --CH2 --), 6.06 (q, 1H, --CH=), 7.22-7.41 (m, 5H, phe). 13C NMR (CDCl3):24.6 (--CH2 --CH2 --CH2 --NH2), 28.1 (--CH2 --CH2 --NH2), 31.9 (--CH2 --CH2 --N<, pyrid), 42.2 (--CH2 --NH2), 50.4 (--CH2 --CH2 --N<, pyrid), 53.3 (=CH--CH2 --N<), 58.3 (>N--CH2 --), 121.9 (>CH--), 124.9 (>CH)2 --), 126.9 (>(CH)2 --), 128.2 (<C=CH--, pyrid), 135.0 (>C=CH--, pyrid), 140.9 (>C<).

Workup

  1. distillationfreshly distilled over sodium)
  2. addition4.5 g of 4-(4-phenyl-1,2,3,6-tetrahydropyridinyl)butyronitrile, in solution in THF, are added dropwise at 0° C.
  3. customreaction
  4. customat 0° C.
  5. customfor 3 hours
  6. filtrationThe precipitate is filtered on celite
  7. dry with materialthe filtrate is dried over anhydrous sodium sulphate
  8. concentrationconcentrated
  9. distillationThe residue is distilled under pump vacuum
  10. customA colourless oil is obtained

Sources & evidence

ORD record
ord-95d78265c3bd40a29fc7eab901a6d91c
Source dataset
uspto-grants-1999_02
Patent number
US05872119

Reaction notes

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