Ammonium Chloride → Diethyl ether 2-propanol

HRID 722682Notes

Reaction equation

HRID 722682 reaction equation
[CH3:1][O:2][C:3](=O)[C:4]1C=CC(CN2CCCCC2)=CC=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl-].[NH4+].[C:26](O)(=O)/C=[CH:28]\[C:29]([OH:31])=O>O1CCCC1.O>[CH2:3]([O:2][CH2:1][CH3:26])[CH3:4].[CH3:1][CH:29]([OH:31])[CH3:28]

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 444266Maleic AcidHCID 782306methyl 4-(piperidin-1-ylmethyl)benzoateHCID 21226445Aluminium lithium hydride

Product 1

HCID 22147583Diethyl ether 2-propanolYield 91%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

4-(Piperidinomethyl)benzoic acid methyl ester (22 mmol) in dry tetrahydrofurane was added dropwise to a suspension of 44 mmol of lithium aluminium hydride in 30 ml of dry tetrahydrofurane at 0° C. After refluxing for 2 hours a saturated solution of ammonium chloride in water was added dropwise. After stirring for 12 hours at ambient temperature the organic layer was isolated and the aqueous layer extracted with methylene chloride. The organic extracts were combined and the solvent was evaporated under reduced pressure. The residue was crystallized with maleic acid from diethyl ether/2-propanol (Yield: 91%). Sodium 4-(piperidinomethyl)benzyl alcoholate (5 mmol) and 6 mmol of 3-phenylpropyl bromide in 10 ml of dry toluene were refluxed for 6 hours. The solvent was evaporated under reduced pressure. The residue was purified by rotatory chromatography on silica gel using methylene chloride/ammonia atmosphere as eluent. The product was crystallized with oxalic acid from diethyl ether/ethanol.

Workup

  1. additionwas added dropwise
  2. customwas isolated
  3. extractionthe aqueous layer extracted with methylene chloride
  4. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-59844546863a432f9ebdf5181c1fd059
Source dataset
uspto-grants-2006_11
Patent number
US07138413B1

Reaction notes

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