Sodium Hydroxide → 2-[1-(3-Methoxybenzyl)piperidin-4-yl]ethylamine

HRID 54551Notes

Reaction equation

HRID 54551 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:17]=[CH:18][CH:19]=1)[C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][NH2:16])[CH2:10][CH2:9]1)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+].S([O-])([O-])(=O)=O.[Mg+2]>O1CCCC1.O.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:17]=[CH:18][CH:19]=1)[CH2:6][N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][NH2:16])[CH2:10][CH2:9]1

Participants

8

Reactant 4

HCID 14798Sodium HydroxideHCID 24083Sulfuric acid magnesium salt (1:1)HCID 199591472-[1-(3-Methoxybenzoyl)piperidin-4-yl]ethylamineHCID 21226445Aluminium lithium hydride

Product 1

HCID 199591902-[1-(3-Methoxybenzyl)piperidin-4-yl]ethylamineYield 42.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 2-[1-(3-methoxybenzoyl)piperidin-4-yl]ethylamine (4.5 g) in tetrahydrofuran (40 ml) was added dropwise to a suspension of lithium aluminum hydride (1.63 g) in tetrahydrofuran (50 ml) under refluxing. After 30 minutes, the mixture was cooled to 0° C., and ethyl acetate (5 ml), water (2 ml), 4N sodium hydroxide (4 ml), water (2 ml) and magnesium sulfate were added thereto successively. The resulting precipitates were removed out by filtration and the filtrate was evaporated in vacuo. The residue was chromagographed on alumina eluting with 2% methanol in chloroform to give 2-[1-(3-methoxybenzyl)piperidin-4-yl]ethylamine (1.8 g) as an oil.

Workup

  1. temperatureunder refluxing
  2. customThe resulting precipitates
  3. customwere removed out by filtration
  4. customthe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-3fab7586478c4e548ab79ab1c26365a4
Source dataset
uspto-grants-1997_04
Patent number
US05622976

Reaction notes

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