Water → Piperidin-3-yl-trityl-amine

HRID 2212178Notes

Reaction equation

HRID 2212178 reaction equation
[C:1]([NH:20][CH:21]1[CH2:26][CH2:25][CH2:24][NH:23][C:22]1=O)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].O.[OH-].[Na+]>O1CCCC1>[NH:23]1[CH2:24][CH2:25][CH2:26][CH:21]([NH:20][C:1]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:22]1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 147292243-(Trityl-amino)-piperidin-2-oneHCID 21226445Aluminium lithium hydride

Product 1

HCID 21963705Piperidin-3-yl-trityl-amineYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Add 3-(trityl-amino)-piperidin-2-one (3.56 g, 10.0 mmol) in portions to a suspension of LiAlH4 (1.00 g, 26.5 mmol) in tetrahydrofuran (25 mL). Heat the reaction to reflux under nitrogen overnight. Cool the reaction to room temperature, add 1.0 mL water, follow by adding 3.0 mL 15% NaOH and 3.0 mL water. Filter the mixture, wash with tetrahydrofuran and concentrate. Patition the material between diethyl ether and water. Add 5.0N sodium hydroxide until the aqueous layer cleared. Extract he product from the aqueous layer with diethyl ether. Dry the combined organic layers over magnesium sulfate and concentrate to give 2.91 g of the title compound as a clear oil, 85% yield. 1H NMR: consistent with structure.

Workup

  1. temperatureHeat
  2. customthe reaction
  3. temperatureto reflux under nitrogen overnight
  4. temperatureCool
  5. customthe reaction to room temperature
  6. filtrationFilter the mixture
  7. washwash with tetrahydrofuran
  8. concentrationconcentrate
  9. additionAdd 5.0N sodium hydroxide until the aqueous layer
  10. extractionExtract he product from the aqueous layer with diethyl ether
  11. dry with materialDry the combined organic layers over magnesium sulfate
  12. concentrationconcentrate

Sources & evidence

ORD record
ord-0c932675f6e94b0e97f9f0e362bb9e40
Source dataset
uspto-grants-2006_09
Patent number
US07101891B2

Reaction notes

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