Water → 1-(2-Phenylethyl)-4-methyl-4-hydroxymethyl-piperidine

HRID 374464Notes

Reaction equation

HRID 374464 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]1([CH2:13][CH2:14][N:15]2[CH2:20][CH2:19][C:18]([CH3:26])([C:21](OCC)=[O:22])[CH2:17][CH2:16]2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.O.[OH-].[Na+]>C1COCC1>[C:7]1([CH2:13][CH2:14][N:15]2[CH2:20][CH2:19][C:18]([CH3:26])([CH2:21][OH:22])[CH2:17][CH2:16]2)[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 18997143HCID 18997143, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 189971411-(2-Phenylethyl)-4-methyl-4-hydroxymethyl-piperidineYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of 0.51 g (13.4 mmol) of lithium aluminum hydride in 20 mL of THF under nitrogen was added dropwise a solution of 3.70 g (13.4 mmol) of 1-(2-phenylethyl)-4-methyl-4-carboethoxypiperidine in 15 mL of THF. The solution was heated at reflux for 3 hours. To the cooled reaction mixture (ice bath) was slowly added 0.5 mL of water, followed by 0.5 mL of 15% sodium hydroxide followed by 1.5 mL of water. The precipitated lithium salts were removed by filtration. The filtrate was evaporated to dryness. The residue was reconstituted in methylene chloride, washed with a small amount of water, dried and evaporated to afford 2.97 g of 1-(2-phenylethyl)-4-methyl-4-hydroxymethyl-piperidine as a yellow oil. NMR (CDCl3) δ7.16-7.23 (m, 5H); 3.40 (s, 2H); 2.79-2.87 (m, 2H); 2.57-2.71 (m, 4H); 2.31-2.42 (m, 2H); 1.57-1.63 (m, 5H); 0.97 (s, 3H).

Workup

  1. temperatureThe solution was heated
  2. temperatureat reflux for 3 hours
  3. customTo the cooled reaction mixture (ice bath)
  4. customThe precipitated lithium salts were removed by filtration
  5. customThe filtrate was evaporated to dryness
  6. washwashed with a small amount of water
  7. customdried
  8. customevaporated

Sources & evidence

ORD record
ord-9d0c5baae47440b693588d284c4ececf
Source dataset
uspto-grants-1996_01
Patent number
US05480892

Reaction notes

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