Tetrahydrofuran → Methyl-[1-(4-ethoxy-phenyl)-piperidin-4-ylmethyl]-amine

HRID 511150Notes

Reaction equation

HRID 511150 reaction equation
C(O[C:6](=O)[NH:7][CH2:8][CH:9]1[CH2:14][CH2:13][N:12]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:22][CH3:23])=[CH:17][CH:16]=2)[CH2:11][CH2:10]1)(C)(C)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].O1CCCC1>O>[CH3:6][NH:7][CH2:8][CH:9]1[CH2:14][CH2:13][N:12]([C:15]2[CH:16]=[CH:17][C:18]([O:21][CH2:22][CH3:23])=[CH:19][CH:20]=2)[CH2:11][CH2:10]1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 21226445Aluminium lithium hydrideHCID 58576345[1-(4-Ethoxy-phenyl)-piperidin-4-ylmethyl]-carbamic acid tert-butyl ester

Product 1

HCID 58576685Methyl-[1-(4-ethoxy-phenyl)-piperidin-4-ylmethyl]-amineYield 98.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

[1-(4-Ethoxy-phenyl)-piperidin-4-ylmethyl]-carbamic acid tert-butyl ester (963 mg, 2.88 mmol, prepared in accordance with Example 106) is added to a molar solution of lithium aluminium hydride in tetrahydrofuran (10 mL, 10 mmol) and the resulting mixture is refluxed for 2 hours. After cooling with an ice bath, water (1 mL) is added carefully and the mixture is stirred overnight at room temperature. The reaction is then filtered and the filtrate is concentrated under reduced pressure. The residue obtained is dried under high vacuum to afford the desired product (701 mg; 2.83 mmol).

Workup

  1. temperaturethe resulting mixture is refluxed for 2 hours
  2. temperatureAfter cooling with an ice bath
  3. filtrationThe reaction is then filtered
  4. concentrationthe filtrate is concentrated under reduced pressure
  5. customThe residue obtained
  6. customis dried under high vacuum

Sources & evidence

ORD record
ord-4ad81030ba29402c833a23fd80857368
Source dataset
uspto-grants-2015_08
Patent number
US09096524B2

Reaction notes

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