Phenyl isocyanate → HCID 54546367, compound

HRID 1419846Notes

Reaction equation

HRID 1419846 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([O:7][C:8]2[CH:15]=[CH:14][C:11]([CH:12]=[O:13])=[CH:10][CH:9]=2)[CH2:3][CH2:2]1.C(N(CC)CC)C.[C:23]1([N:29]=[C:30]=[O:31])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>O1CCCC1.CCOC(C)=O>[NH:29]([C:30]([N:1]1[CH2:2][CH2:3][CH:4]([O:7][C:8]2[CH:15]=[CH:14][C:11]([CH:12]=[O:13])=[CH:10][CH:9]=2)[CH2:5][CH2:6]1)=[O:31])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 3

HCID 7672Phenyl isocyanateHCID 8471TriethylamineHCID 450368384-[(Piperidin-4-yl)oxy]benzaldehyde

Product 1

HCID 54546367HCID 54546367, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To an ice cooled solution of 4-(piperidin-4-yloxy)benzaldehyde (2 g) and triethylamine (1.35 ml) in tetrahydrofuran (20 ml) was added phenyl isocyanate (1.3 ml). The mixture was stirred at room temperature for 3 h. At the end of this time, the reaction mixture was diluted with EtOAc, washed with aqueous NaHCO3 solution followed by water, dried (Na2SO4) and concentrated to get 3.1 g (99%) of the title product as a gummy solid.

Workup

  1. washwashed with aqueous NaHCO3 solution
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-6f1bee5fc90b4b60854eb4296b00cace
Source dataset
uspto-grants-1999_03
Patent number
US05889025

Reaction notes

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