Aluminum(III) Chloride → HCID 19420759, compound

HRID 863856Notes

Reaction equation

HRID 863856 reaction equation
[Cl-:1].[Al+3].[Cl-].[Cl-].[H-].[Al+3].[Li+].[H-].[H-].[H-].[O:11]1[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[N:13]=[C:12]1[C:20]1[CH:28]=[CH:27][C:23]([CH2:24][C:25]#[N:26])=[CH:22][CH:21]=1>CCOCC.C1COCC1>[ClH:1].[O:11]1[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[N:13]=[C:12]1[C:20]1[CH:28]=[CH:27][C:23]([CH2:24][CH2:25][NH2:26])=[CH:22][CH:21]=1

Participants

6

Reactant 3

HCID 6451240Aluminum(III) ChlorideHCID 19420771HCID 19420771, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 19420759HCID 19420759, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
20 °C

Procedure

Aluminum chloride (0.2 g; 1.5 mmol) is added to a suspension of lithium aluminum hydride (60 mg; 1.5 mmol) in dry ether (6 ml) at 0° C. The reaction is stirred for 10 minutes at 20° C. and cooled to 0° C. A solution of 4-(benzoxazol-2-yl)benzyl cyanide (0.24 g; 1.02 mmol) in dry THF (4 ml) is added dropwise and the reaction is stirred at 20° C. for 2 hours. The reaction is quenched with H2O, diluted with ether and washed vigorously with 2N HCl. The ether is decanted and the aqueous layer is washed with ether. The aqueous phase is neutralized with 15% NaOH and extracted with CH2Cl2. The extracts are concentrated and purified with column chromatography using CH2Cl2 to 20% MeOH/CH2Cl2. The product is acidified with acidic methanol and concentrated to yield 2-[4-(benzoxazol-2-yl)phenyl]-1-ethanamine hydrochloride (m.p. 250° C. dec.).

Workup

  1. temperaturecooled to 0° C
  2. stirringthe reaction is stirred at 20° C. for 2 hours
  3. customThe reaction is quenched with H2O
  4. additiondiluted with ether
  5. washwashed vigorously with 2N HCl
  6. customThe ether is decanted
  7. washthe aqueous layer is washed with ether
  8. extractionextracted with CH2Cl2
  9. concentrationThe extracts are concentrated
  10. custompurified with column chromatography
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-d111ea93fb5a453eaddeaf9b686d0f7f
Source dataset
uspto-grants-1996_10
Patent number
US05561143

Reaction notes

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