Aluminium lithium hydride → 3-Cyclopentyloxy-4-methoxyphenethylamine

HRID 275488

Reaction equation

HRID 275488 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH:7]1([O:12][C:13]2[CH:14]=[C:15]([CH:21]=[CH:22][C:23]=2[O:24][CH3:25])[CH:16]=[CH:17][N+:18]([O-])=O)[CH2:11][CH2:10][CH2:9][CH2:8]1>CCOCC.O1CCCC1>[CH:7]1([O:12][C:13]2[CH:14]=[C:15]([CH2:16][CH2:17][NH2:18])[CH:21]=[CH:22][C:23]=2[O:24][CH3:25])[CH2:8][CH2:9][CH2:10][CH2:11]1

Participants

5

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 545032242-(Cyclopentyloxy)-1-methoxy-4-(2-nitroethenyl)benzene

Product 1

HCID 112763943-Cyclopentyloxy-4-methoxyphenethylamineYield 81%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of lithium aluminum hydride (10.83 g, 28.5 mmol) in ether (250 mL) at 0° C. under an argon atmosphere was added dropwise a solution of 3-cyclopentyloxy-4-methoxy-β-nitrostyrene (15.00 g, 57.0 mmol) in tetrahydrofuran (85 mL). The resulting mixture was allowed to warm to room temperature and stirred overnight. The reaction mixture was cooled to 0° C. and quenched by the successive dropwise addition of water (11 mL), 15% sodium hydroxide (11 mL) and water (33 mL). The mixture was filtered through a pad of Celite™ and the filtrate was washed successively with water, 10% hydrochloric acid and water. The aqueous washes were combined, made basic with saturated aqueous potassium carbonate and extracted three times with ether and twice with methylene chloride. The organic layers were combined and dried (potassium carbonate). Removal of the solvent in vacuo provided the amine (10.80 g, 81%). A portion of the crude amine was purified by flash chromatography, eluting with 1:10:90 water/methanol/chloroform.

Workup

  1. temperatureThe reaction mixture was cooled to 0° C.
  2. customquenched by the successive dropwise addition of water (11 mL), 15% sodium hydroxide (11 mL) and water (33 mL)
  3. filtrationThe mixture was filtered through a pad of Celite™
  4. washthe filtrate was washed successively with water, 10% hydrochloric acid and water
  5. extractionextracted three times with ether
  6. dry with materialdried (potassium carbonate)
  7. customRemoval of the solvent in vacuo

Sources & evidence

ORD record
ord-940e1276a546428c810a1f12135aa62c
Source dataset
uspto-grants-1995_02
Patent number
US05393788

Linked notes

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