Aluminium lithium hydride → 3-(1,3-Benzodioxol-5-yloxymethyl)-4-(4-fluorophenyl)piperidine

HRID 2296772Notes

Reaction equation

HRID 2296772 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[F:7][C:8]1[CH:13]=[CH:12][C:11]([CH:14]2[CH2:19][C:18](=O)[NH:17][CH2:16][CH:15]2[CH2:21][O:22][C:23]2[CH:28]=[CH:27][C:26]3[O:29][CH2:30][O:31][C:25]=3[CH:24]=2)=[CH:10][CH:9]=1>O1CCCC1>[F:7][C:8]1[CH:13]=[CH:12][C:11]([CH:14]2[CH2:19][CH2:18][NH:17][CH2:16][CH:15]2[CH2:21][O:22][C:23]2[CH:28]=[CH:27][C:26]3[O:29][CH2:30][O:31][C:25]=3[CH:24]=2)=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 227338424-(4-Fluorophenyl)-3-[(3,4-methylenedioxyphenyl)oxymethyl]piperidine-6-one

Product 1

HCID 46913-(1,3-Benzodioxol-5-yloxymethyl)-4-(4-fluorophenyl)piperidineYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of lithium aluminium hydride in tetrahydrofuran (1.0M solution, 2 ml, 2.0 mmol) was added over ten minutes to a well stirred solution of 4-(4-fluorophenyl)-3-[(3,4-methylenedioxyphenyl)oxymethyl]piperidine-6-one (0.41 g, (0.96 mmol) in tetrahydrofuran (7 ml), maintaining the temperature below 25° C. The reaction solution was stirred for 2 hours and then quenched first of all with water (0.16 ml), then with 15% aqueous sodium hydroxide solution (0.1 ml), and finally with water again (0.4 ml). The reaction mixture was stirred for 0.5 hours to complete the precipitation, diluted with dichloromethane (30 ml) and filtered. The filtrate was evaporated in vacuo to give the title product with a trans/cis ratio=72:28. Yield 90%.

Workup

  1. temperaturemaintaining the temperature below 25° C
  2. customquenched first of all with water (0.16 ml)
  3. stirringThe reaction mixture was stirred for 0.5 hours
  4. customthe precipitation
  5. additiondiluted with dichloromethane (30 ml)
  6. filtrationfiltered
  7. customThe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-b636df5d747942cfb796fceb7f3104d9
Source dataset
uspto-grants-2002_12
Patent number
US06489347B1

Reaction notes

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