Hydrochloric Acid → HCID 18670134, compound

HRID 1059326Notes

Reaction equation

HRID 1059326 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][C:15]([CH3:20])([CH3:19])[CH2:16][C:17]#[N:18])[CH2:10][CH2:9]1)=O)(C)(C)C.[ClH:21]>O1CCCC1>[ClH:21].[NH:8]1[CH2:13][CH2:12][CH:11]([CH2:14][C:15]([CH3:20])([CH3:19])[CH2:16][C:17]#[N:18])[CH2:10][CH2:9]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 18670486HCID 18670486, compound

Product 1

HCID 18670134HCID 18670134, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6.7 g of 4-[1-(tert-butoxycarbonyl)-piperidin-4-yl]-3,3-dimethylbutyronitrile in 50 ml of tetrahydrofuran was added at room temperature 20 ml of conc. hydrochloric acid and the resulting mixture was stirred for 2 hours. Then the reaction mixture was concentrated under reduced pressure to thereby give crude 4-(piperidin-4-yl)-3,3-dimethylbutyronitrile hydrochloride. This crude product was dissolved in 100 ml of dichloromethane. After adding 10.5 g of anhydrous potassium carbonate and 3.3 ml of benzyl bromide, the reaction mixture was reacted at room temperature for 12 hours. After adding water, the reaction mixture was extracted with ethyl acetate, washed with a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. After distilling off the solvent under reduced pressure, the residue was purified by silica gel column chromatography (eluted with n-hexane/ethyl acetate) to thereby give 4.7 g of the title compound as a colorless oily substance.

Workup

  1. concentrationThen the reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-09a1a6309d404de99f46962498d68370
Source dataset
uspto-grants-2003_02
Patent number
US06518423B1

Reaction notes

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