Hydrochloric Acid → (+/-)-1-(1-Amino-3-butyl)-4-(4-fluorophenyl)piperidine

HRID 429058Notes

Reaction equation

HRID 429058 reaction equation
[C:1]([CH2:3][CH:4]([N:6]1[CH2:11][CH2:10][CH:9]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)[CH2:8][CH2:7]1)[CH3:5])#[N:2].B.O1CCCC1.Cl.[OH-].[Na+]>O1CCCC1>[NH2:2][CH2:1][CH2:3][CH:4]([N:6]1[CH2:7][CH2:8][CH:9]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)[CH2:10][CH2:11]1)[CH3:5]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 2723981Borane;tetrahydrofuranHCID 911828683-[4-(4-Fluorophenyl)piperidin-1-yl]butanenitrile

Product 1

HCID 91338801(+/-)-1-(1-Amino-3-butyl)-4-(4-fluorophenyl)piperidine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of (+/−)-1-(1-cyano-2-propyl)-4-(4-fluorophenyl)piperidine (457 mg, 1.85 mmol) in tetrahydrofuran (5 mL) was added dropwise to 1 M borane/tetrahydrofuran (5 mL) under an inert argon atmosphere. The reaction mixture was refluxed for two hours and then cooled to ambient temperature. 6 N HCl (4 mL) was added to the reaction, stirred for 0.5 hour and then the tetrahydrofuran boiled off. The resultant aqueous solution was cooled in an ice bath and made basic by addition solid sodium hydroxide pellets. The product was extracted into methylene chloride, the extract dried (anhydrous sodium sulfate), filtered, and the solvent removed to give the title compound as a colorless oil.

Workup

  1. temperatureThe reaction mixture was refluxed for two hours
  2. temperatureThe resultant aqueous solution was cooled in an ice bath
  3. extractionThe product was extracted into methylene chloride
  4. dry with materialthe extract dried (anhydrous sodium sulfate)
  5. filtrationfiltered
  6. customthe solvent removed

Sources & evidence

ORD record
ord-e59753223df547fe98a587abbccc430b
Source dataset
uspto-grants-2001_11
Patent number
US06316437B1

Reaction notes

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