Hydrochloric Acid → N,N'-Dimethyl-N-[4-(piperidin-1-yl)but-2-yn-1-yl]urea

HRID 704550Notes

Reaction equation

HRID 704550 reaction equation
[CH3:1][N:2]([CH2:7][C:8]#[CH:9])[C:3]([NH:5][CH3:6])=[O:4].[CH2:10]=O.[NH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1.Cl>O1CCOCC1>[CH3:1][N:2]([CH2:7][C:8]#[C:9][CH2:10][N:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)[C:3]([NH:5][CH3:6])=[O:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 8082PiperidineHCID 15669664HCID 15669664, compound

Product 1

HCID 15167054N,N'-Dimethyl-N-[4-(piperidin-1-yl)but-2-yn-1-yl]urea

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of N,N'-dimethyl-N-(2-propynyl)urea (2.5 g, 0.02 mol) (Example A), paraformaldehyde (0.6 g, 0.02 mol), piperidine (1.7 g, 0.02 mol), and a spatula tip of cuprous chloride in 150 ml of anhydrous dioxane is allowed to reflux for two hours. After cooling the solution is made strongly acidic with a 2N solution of hydrochloric acid and washed with diethyl ether. The aqueous solution is then made basic by the addition of solid potassium carbonate until saturated, followed by extraction with diethyl ether (2X). The diethyl ether solution is dried over magnesium sulfate, filtered, and concentrated to afford a yellow oil. Nuclear Magnetic Resonance (NMR) (CDCl3): 4.81 (brs, 1H); 4.11 (t, J=1.9 Hz, 2H); 3.24 (t, J=1.9 Hz, 2H); 2.93 (s, 3H); 2.81 (d, J=4.4 Hz, 3H); 2.48 (m, 4H); 1.63 (m, 6H).

Workup

  1. temperatureto reflux for two hours
  2. temperatureAfter cooling the solution
  3. washwashed with diethyl ether
  4. additionThe aqueous solution is then made basic by the addition of solid potassium carbonate until saturated,
  5. extractionfollowed by extraction with diethyl ether (2X)
  6. dry with materialThe diethyl ether solution is dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto afford a yellow oil

Sources & evidence

ORD record
ord-853079e7c2a142ea894b16def0611462
Source dataset
uspto-grants-1991_01
Patent number
US04988688

Reaction notes

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