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

HRID 2220837Notes

Reaction equation

HRID 2220837 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 (55 mL of a 1M solution in THF, 0.055 mol) was added drop wise to a solution of II (7.6 g, 0.037 mol) in dry THF (70 mL) at 0° C. and stirred overnight at room temperature in an argon atmosphere. The reaction 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 III. The purity of III (99%) was determined by GC. 1H NMR (360 MHz, DMSO-d6) δ 1.34 (m, 2H), 1.54 (m, 2H), 2.51 (m, 4H), 3.70 (s, 3H), 6.83 (d, J=8.6 Hz, 2H), 7.08 (d, J=8.3 Hz, 2H); 13C (90 MHz, DMSO-d6) δ 28.6, 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-fe7639d0c12847729ca86db3f146eb51
Source dataset
uspto-grants-2008_05
Patent number
US07368450B2

Reaction notes

Loading…