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

HRID 2188422Notes

Reaction equation

HRID 2188422 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][CH2:16][C:17]([NH2:19])=O)=[CH:10][CH:9]=1.O.[OH-].[Na+]>C(OCC)C.C1COCC1>[Cl:7][C:8]1[CH:9]=[CH:10][C:11]([CH2:14][CH2:15][CH2:16][CH2:17][NH2:19])=[CH:12][CH:13]=1

Participants

7

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 110743574-(4-Chlorophenyl)butanamideHCID 21226445Aluminium lithium hydride

Product 1

HCID 107738224-(4-Chlorophenyl)butan-1-amineYield 95%

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 (2.40 g, 63.2 mmol) in 65 mL diethyl ether was added slowly a solution of (3.12 g 15.8 mmol) of 36a in 28 mL THF, and stirred at rt for 1 h. To the reaction mixture was slowly added 4 mL water, 4 mL 5 N NaOH(aq), and 12 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 37a (2.76 g, 95%) as an oil. UV λmax 224 (7600, 95% ETHANOL). 1H NMR (400 MHz, CDCl3) δ 7.23 (m, 2H), 7.10 (d, J=8 Hz, 2H), 2.74 (t, J=7 Hz, 2H), 2.60 (t, J=8 Hz, 2H), 2.25 (s, 2H), 1.64 (m, 2H), 1.49 (m, 2H). 13C NMR (CDCl3) δ 141.2, 131.8, 130.1, 128.8, 42.3, 35.4, 33.6, 29.0; IR (liq.) 3365 (b), 3296 (b), 3026, 2933 (s), 2858 (s), 2170 (w), 1996 (w), 1576, 1492 (s), 1460, 1093 (s), 1016 (s), 831, 821, 804, cm−1; HRMS (FAB) calcd for C10H14ClN+H1 184.0893, found 184.0879.

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-8c0dde15cd324d83a75b226b019f7202
Source dataset
uspto-grants-2002_06
Patent number
US06410585B1

Reaction notes

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