Water → 4-(4-Methoxyphenyl)butan-1-amine

HRID 2188423Notes

Reaction equation

HRID 2188423 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][CH2:17][C:18]([NH2:20])=O)=[CH:11][CH:10]=1.O.[OH-].[Na+]>C(OCC)C.C1COCC1>[CH3:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][CH2:17][CH2:18][NH2:20])=[CH:11][CH:10]=1

Participants

7

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 225661754-(4-Methoxyphenyl)butanamide

Product 1

HCID 105835064-(4-Methoxyphenyl)butan-1-amineYield 98.1%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

(Ali, F. E.; Dandridge, P. A.; Gleason, J. G.; Krell, R. D.; Kruse, C. H.; Lavanchy, P. G; Snader, K. M. J. Med Chem., 1982, 25, 947). To a stirred suspension of lithium aluminum hydride (4.40 g, 116 mmol) in 120 mL diethyl ether was added dropwise a solution of 36b (5.60 g, 29.0 mmol) in 10 mL THF, and stirred at rt for 1 h. To the reaction mixture was added 7.5 mL water, 7.5 mL 5 N NaOH(aq), and 20 mL water. The organics were removed from the emulsion which was dissolved in water and extracted with ether. The organic portions were dried over Na2SO4(s), and condensed to give 37b (5.10 g, 98%) as an oil. UV λmax 223 (9410, 95% EtOH). (400 MHz, CDCl3) δ 7.10 (d, J=9 Hz, 2H), 6.83 (d, J=9 Hz, 2H), 3.79 (s, 3H), 2.71 (t, J=7 Hz, 2H), 2.58 (t, J=7 Hz, 2H), 1.63 (m, 2H), 1.48 (m, 2H); IR (liq.) 2933 (s), 2856, 2145 (w), 2059 (w), 1996 (w), 1612 (s), 1584, 1513 (s), 1461, 1442, 1246 (s), 1178, 1034 (s), 827, 822, cm−1. 1HRMS (FAB) calcd for C11H17NO+H1 180.1388, found 180.1387.

Workup

  1. customThe organics were removed from the emulsion which
  2. dissolutionwas dissolved in water
  3. extractionextracted with ether
  4. dry with materialThe organic portions were dried over Na2SO4(s), and condensed

Sources & evidence

ORD record
ord-b8b0dd67dc3147ae9bda1e023f0316f2
Source dataset
uspto-grants-2002_06
Patent number
US06410585B1

Reaction notes

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