(1,4'-Bipiperidine)-4'-carboxamide → HCID 22185336, compound

HRID 1795178Notes

Reaction equation

HRID 1795178 reaction equation
[N:1]1([C:7]2([C:13](N)=[O:14])[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Na]>C(O)CC.CCCCCC>[N:1]1([C:7]2([CH2:13][OH:14])[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 96486(1,4'-Bipiperidine)-4'-carboxamideHCID 5360545Sodium

Product 1

HCID 22185336HCID 22185336, compoundYield 93.6%

Reagents, catalysts & solvents 2

HCID 10311-PropanolSolventHCID 8058HexaneSolvent

Procedure

In a three neck round-bottom flask equipped with a stirring bar, reflux condenser, and rubber septa is placed [1,4′]bipiperidinyl-4′-carboxylic acid amide (5.01 g, 23.7 mmol) in 140 mL of anhydrous 1-propanol and the solution is heated to reflux. Sodium metal (˜9.276 g, 403.4 mmol) rinsed in hexane to remove mineral oil) is added in portions. Once the sodium metal completely dissolves, the mixture is allowed to stir over the weekend. The reaction mixture is cooled to room temperature and the solvent removed under reduced pressure. Distilled water is added and the solution extracted with chloroform. The organic layer is collected, dried over sodium sulfate, filtered, and the solvent removed under reduced pressure to afford 4.4 g of the desired product which is used without further purification. 1H NMR (CD3OD, 300 MHz) δ 1.48–1.60 (m, 8H), 1.72–1.80 (m, 2H), 2.61–2.71 (m, 6H), 2.92–3.01 (m, 2H), 3.37 (s, 1H), 3.56 (s, 2H). MS (ESI) m/z 199 (M+H+).

Workup

  1. customIn a three neck round-bottom flask equipped with a stirring bar
  2. temperaturereflux condenser
  3. temperaturethe solution is heated to reflux
  4. customto remove mineral oil)
  5. additionis added in portions
  6. dissolutionOnce the sodium metal completely dissolves
  7. customthe solvent removed under reduced pressure
  8. additionDistilled water is added
  9. extractionthe solution extracted with chloroform
  10. customThe organic layer is collected
  11. dry with materialdried over sodium sulfate
  12. filtrationfiltered
  13. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-d6bdb78d73c94048ba8189898864043c
Source dataset
uspto-grants-2006_04
Patent number
US07026335B2

Reaction notes

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