2-Propylpiperidine → 4-(2-Propyl-piperidin-1-yl)-butyronitrile

HRID 1859623

Reaction equation

HRID 1859623 reaction equation
[CH2:1]([CH:4]1[CH2:9][CH2:8][CH2:7][CH2:6][NH:5]1)[CH2:2][CH3:3].Br[CH2:11][CH2:12][CH2:13][C:14]#[N:15].C(=O)([O-])[O-].[K+].[K+].C(Cl)Cl.CO>C(#N)C.[Cl-].[Na+].O>[CH2:1]([CH:4]1[CH2:9][CH2:8][CH2:7][CH2:6][N:5]1[CH2:11][CH2:12][CH2:13][C:14]#[N:15])[CH2:2][CH3:3]

Participants

7

Reactant 4

HCID 99852-PropylpiperidineHCID 11430Potassium CarbonateHCID 214124-BromobutyronitrileHCID 21226129Dichloromethane methanol

Product 1

HCID 186263224-(2-Propyl-piperidin-1-yl)-butyronitrileYield 83%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A mixture of 2-propylpiperidine (550 mg, 4.3 mmol), 4-bromobutyronitrile (430 mg, 3.0 mmol) and potassium carbonate (550 mg, 4.0 mmol) in acetonitrile (5 mL) was stirred at rt for 12 h., followed by addition of a saturated brine (25 mL). The reaction mixture was extracted with ethyl acetate (3×25 mL) and the combined organic phases were dried (MgSO4) and evaporated to dryness to produce crude 8. The crude product was subjected to CC [eluent: CH2Cl2: MeOH (99: 1)] to give pure 8 (0.48 g, 83%); LC-MS [M+H]+194 (cald. 194.2).

Workup

  1. extractionThe reaction mixture was extracted with ethyl acetate (3×25 mL)
  2. dry with materialthe combined organic phases were dried (MgSO4)
  3. customevaporated to dryness
  4. customto produce crude 8

Sources & evidence

ORD record
ord-b0ad0b4a84f843378a0a9731812c0337
Source dataset
uspto-grants-2003_03
Patent number
US06528529B1

Linked notes

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