Water → N-[2-(4-methoxyphenyl)-1-methylethyl]-N-ethyl-(piperidin-4-ylmethyl)amine

HRID 429823Notes

Reaction equation

HRID 429823 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH:16]([N:18]([C:21]([CH:23]2[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]2)=O)[CH2:19][CH3:20])[CH3:17])=[CH:11][CH:10]=1.O>O1CCCC1>[CH3:7][O:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:15][CH:16]([N:18]([CH2:21][CH:23]2[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]2)[CH2:19][CH3:20])[CH3:17])=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 962WaterHCID 18353004N-[2-(4-methoxyphenyl)-1-methylethyl]-N-ethyl-(piperidin-4-ylcarbonyl)amineHCID 21226445Aluminium lithium hydride

Product 1

HCID 18352857N-[2-(4-methoxyphenyl)-1-methylethyl]-N-ethyl-(piperidin-4-ylmethyl)amine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of lithium aluminum hydride (30 mmole) in tetrahydrofuran (120 ml) was heated under reflux. A solution of N-[2-(4-methoxyphenyl)-1-methylethyl]-N-ethyl-(piperidin-4-ylcarbonyl)amine (7.8 grams, 25.6 mmole) in tetrahydrofuran (40 ml) was added dropwise. After 30 minutes excess water was added at 22° C. The mixture was filtered and the filtrate was concentrated under reduced pressure to give N-[2-(4-methoxyphenyl)-1-methylethyl]-N-ethyl-(piperidin-4-ylmethyl)amine, which was isolated as the hydrochloride salt from acetonitrile (7.0 grams, 75%), m.p. 144-146° C., M+H 405.

Workup

  1. temperatureunder reflux
  2. filtrationThe mixture was filtered
  3. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-54bd9a6fc9a646eeb5caf93d9502fd84
Source dataset
uspto-grants-2001_11
Patent number
US06319920B1

Reaction notes

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