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

HRID 25094Notes

Reaction equation

HRID 25094 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][CH2:18][N:19]=[N+]=[N-])=[CH:11][CH:10]=1.O>C1COCC1>[CH3:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][CH2:17][CH2:18][NH2:19])=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 962WaterHCID 114994244-(4-Methoxyphenyl)butylazideHCID 21226445Aluminium lithium hydride

Product 1

HCID 105835064-(4-Methoxyphenyl)butan-1-amineYield 94%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Lithium aluminum hydride (LAH) (55 mL of a 1.0 M solution in THF, 0.055 mol) was added drop wise to a solution of 2 (7.6 g, 0.037 mol) in dry THF (70 mL) at 0° C. The mixture was stirred overnight at room temperature in an argon atmosphere then the mixture was treated with water (1.5 mL), then 15% NaOH (1.5 mL), then with more water (3 mL) and filtered. The solid precipitate was washed with THF. The combined organic fractions were dried over magnesium sulfate and the solvent was removed under reduced pressure to give 6.2 g (94%) of 3. The purity of 3 (99%) was determined by GC. 1H NMR (360 MHz, DMSO-d6) δ1.34 (m, 2H), 1.54 (m, 2H), 2.51 (m, 4H), 3.70 (s, 3H), 6.83 (d, 2H), 7.08 (d, 2H). 13C (90 MHz, DMSO-d6) δ28.6, 330, 34.1, 41.5, 54.8, 113.1, 129.1, 132.2, 157.3

Workup

  1. filtration15% NaOH (1.5 mL), then with more water (3 mL) and filtered
  2. washThe solid precipitate was washed with THF
  3. dry with materialThe combined organic fractions were dried over magnesium sulfate
  4. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-675c5674960d4181840654e3a1090d96
Source dataset
uspto-grants-2005_02
Patent number
US06858614B2

Reaction notes

Loading…