Water → HCID 23366916, compound

HRID 1079408Notes

Reaction equation

HRID 1079408 reaction equation
C(O[C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:20]=[CH:19][C:18]([NH:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].O>O1CCCC1>[CH2:22]([NH:21][C:18]1[CH:19]=[CH:20][C:15]([O:14][CH:11]2[CH2:10][CH2:9][N:8]([CH3:6])[CH2:13][CH2:12]2)=[CH:16][CH:17]=1)[CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]

Participants

5

Reactant 3

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 23366973HCID 23366973, compound

Product 1

HCID 23366916HCID 23366916, compoundYield 79.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the compound of Example 68 (1.5 g) in tetrahydrofuran (20 ml) was added lithium aluminum hydride (0.15 g) and the mixture was heated under reflux for hours. Water was added to the mixture and the precipitate formed was filtered off and the filtrate was concentrated. The residue was purified by silica gel column chromatography (developing solvent: methylene chloride/methanol=10/1 (v/v)) to obtain 4-(4-hexylaminophenyloxy)-1-methylpiperidine (0.92 g) as a brown oil. The oil was dissolved in ethanol (20 ml), conc. hydrochloric acid (0.53 ml) was added to the solution and the solvent was distilled off to leave a solid. The solid was recrystallized from ethanol/ethyl ether to obtain 4-(4-hexylaminophenyloxy)-1-methylpiperidine dihydrochloride (0.76 g) as white crystals, m.p. 163°-172° C.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for hours
  3. customthe precipitate formed
  4. filtrationwas filtered off
  5. concentrationthe filtrate was concentrated
  6. customThe residue was purified by silica gel column chromatography (developing solvent: methylene chloride/methanol=10/1 (v/v))

Sources & evidence

ORD record
ord-1ba26410bf1c43bcb13775c6efe524ca
Source dataset
uspto-grants-1996_12
Patent number
US05580883

Reaction notes

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