Piperidine → HCID 57931197, compound

HRID 551145Notes

Reaction equation

HRID 551145 reaction equation
[C-:1]#[N:2].[Na+].[NH:4]1[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1.[CH2:10]([S:13]([N:16]1[CH2:21][CH2:20][C:19](=O)[CH2:18][CH2:17]1)(=[O:15])=[O:14])[CH2:11][CH3:12].[OH-].[Na+]>Cl.CO>[CH2:10]([S:13]([N:16]1[CH2:21][CH2:20][C:19]([C:1]#[N:2])([N:4]2[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]2)[CH2:18][CH2:17]1)(=[O:15])=[O:14])[CH2:11][CH3:12]

Participants

7

Reactant 4

HCID 8082PiperidineHCID 8929Sodium CyanideHCID 14798Sodium HydroxideHCID 208851121-(Propane-1-sulfonyl)piperidin-4-one

Product 1

HCID 57931197HCID 57931197, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

Sodium cyanide (0.98 g, 20.0 mmol) was added to a solution of piperidine (1.98 ml, 20.0 mmol) in 1 N hydrochloric acid (20 mL). A solution of 1-(propylsulfonyl)piperidin-4-one (4.11 g, 20.0 mmol) in methanol (40 mL) was added dropwise to the mixture over 30 min. On complete addition the mixture was allowed to warm to ambient temperature and stirred for 18 h. The precipitate was filtered and washed with water (10 mL) and dried under high vacuum at 60° C. which gave a white solid. The volume of the filtrate was reduced to approx 20 mL and the pH of the aqueous residue was adjusted to 7 by the addition of 4 N sodium hydroxide solution. The aqueous phase was extracted with ethyl acetate (2×100 mL) and dichloromethane (2×100 mL). The combined organics were dried over anhydrous sodium sulfate, filtered and evaporated to give 1′-(propylsulfonyl)-1,4′-bipiperidine-4′-carbonitrile as a colourless oil. 1H NMR (400 MHz, CDCl3): δ 3.70-3.64 (m, 2 H); 3.09-3.03 (m, 2 H); 2.85-2.81 (m, 2 H); 2.51 (t, J=5.0 Hz, 4 H); 2.15 (d, J=13.6 Hz, 2 H); 1.83-1.75 (m, 4 H); 1.58-1.54 (m, 4 H); 1.45-1.39 (m, 2 H); 1.00 (t, J=7.5 Hz, 3 H).

Workup

  1. additionOn complete addition the mixture
  2. filtrationThe precipitate was filtered
  3. washwashed with water (10 mL)
  4. customdried under high vacuum at 60° C. which
  5. customgave a white solid
  6. extractionThe aqueous phase was extracted with ethyl acetate (2×100 mL) and dichloromethane (2×100 mL)
  7. dry with materialThe combined organics were dried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-4c32cbc80d7345feb851f3afa87ab649
Source dataset
uspto-grants-2011_05
Patent number
US07947714B2

Reaction notes

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