Water → HCID 69053917, compound

HRID 1727212Notes

Reaction equation

HRID 1727212 reaction equation
[C:1]1([CH2:7][N:8]2[CH2:13][CH2:12][CH:11]([OH:14])[CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:15][CH2:16][CH2:17][CH2:18][N:19]=[C:20]=[O:21].O>O1CCOCC1>[CH2:18]([NH:19][C:20](=[O:21])[O:14][CH:11]1[CH2:12][CH2:13][N:8]([CH2:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:9][CH2:10]1)[CH2:17][CH2:16][CH3:15]

Participants

5

Reactant 3

HCID 962WaterHCID 8110Butyl isocyanateHCID 784611-Benzylpiperidin-4-ol

Product 1

HCID 69053917HCID 69053917, compoundYield 92.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

1-(Phenylmethyl)piperidin-4-ol (10 g, 52.2 mmol) was stirred in dioxane (90 ml) at room temperature. N-butyl isocyanate (5.0 g, 52.2 mmol) in dioxane (10 ml) was added and the reaction mixture was heated under reflux for 24 h. Water (20 ml) was added and the reaction mixture was concentrated in vacuo to give a brown oil. The crude product was partitioned between diethyl ether and water and the organic extracts were dried (MgSO4) to give the title compound as an oil (14 g, 92%).

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureunder reflux for 24 h
  3. concentrationthe reaction mixture was concentrated in vacuo
  4. customto give a brown oil
  5. customThe crude product was partitioned between diethyl ether and water
  6. dry with materialthe organic extracts were dried (MgSO4)

Sources & evidence

ORD record
ord-1ffa4d3e4fc34845ade4b349247615de
Source dataset
uspto-grants-2009_02
Patent number
US07494992B2

Reaction notes

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