Water → 1-(2-Phenylethyl)-4-methyl-4-hydroxymethyl-piperidine
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]=1Participants
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-(2phenylethyl)-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
- temperatureThe solution was heated
- temperatureat reflux for 3 hours
- customTo the cooled reaction mixture (ice bath)
- customThe precipitated lithium salts were removed by filtration
- customThe filtrate was evaporated to dryness
- washwashed with a small amount of water
- customdried
- customevaporated
Sources & evidence
- ORD record
- ord-c7ac832383fc44d68a965bb91c289bc3
- Source dataset
- uspto-grants-1994_10
- Patent number
- US05356906
Reaction notes
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