Aluminium lithium hydride → 1-[2-(2-Fluorophenoxy)-ethyl]-4-[3-(3,4,5-trimethoxyphenyl)propyl]-piperazine dihydrochloride

HRID 1928548

Reaction equation

HRID 1928548 reaction equation
[ClH:1].[F:2][C:3]1[CH:33]=[CH:32][CH:31]=[CH:30][C:4]=1[O:5][CH2:6][CH2:7][N:8]1[CH2:13][CH2:12][N:11]([C:14](=O)[CH2:15][CH2:16][C:17]2[CH:22]=[C:21]([O:23][CH3:24])[C:20]([O:25][CH3:26])=[C:19]([O:27][CH3:28])[CH:18]=2)[CH2:10][CH2:9]1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[ClH:1].[ClH:1].[F:2][C:3]1[CH:33]=[CH:32][CH:31]=[CH:30][C:4]=1[O:5][CH2:6][CH2:7][N:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][C:17]2[CH:22]=[C:21]([O:23][CH3:24])[C:20]([O:25][CH3:26])=[C:19]([O:27][CH3:28])[CH:18]=2)[CH2:10][CH2:9]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 672988021-{4-[2-(2-Fluorophenoxy)ethyl]piperazin-1-yl}-3-(3,4,5-trimethoxyphenyl)propan-1-one hydrochloride

Product 1

HCID 672992191-[2-(2-Fluorophenoxy)-ethyl]-4-[3-(3,4,5-trimethoxyphenyl)propyl]-piperazine dihydrochlorideYield 173.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-{4-[2-(2-fluorophenoxy)ethyl]piperazin-1-yl}-3-(3,4,5-trimethoxyphenyl)-propan-1-one hydrochloride (0.2 g, 0.41 mmol) in THF (50 mL) was added LiAlH4 (0.2 g, 5 mmol). The reaction mixture was stirred under N2 for a day, cooled with an ice bath, and quenched with water (0.2 mL) and 10N NaOH aqueous solution (0.2 mL). The solid was filtered and the filtrate was concentrated to dryness. The residue was treated with ether and 2N HCl in ether (2 mL). The white solid was filtered and dried under vacuum to yield the title compound (0.18 g, 87%).

Workup

  1. temperaturecooled with an ice bath
  2. customquenched with water (0.2 mL) and 10N NaOH aqueous solution (0.2 mL)
  3. filtrationThe solid was filtered
  4. concentrationthe filtrate was concentrated to dryness
  5. additionThe residue was treated with ether and 2N HCl in ether (2 mL)
  6. filtrationThe white solid was filtered
  7. customdried under vacuum

Sources & evidence

ORD record
ord-51b4db710de04d45974849d18197797c
Source dataset
uspto-grants-2012_05
Patent number
US08183374B2

Linked notes

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