Triethylamine → HCID 18630643, compound

HRID 582557Notes

Reaction equation

HRID 582557 reaction equation
[OH:1][CH2:2][CH2:3][NH:4][CH:5]1[CH2:10][CH2:9][N:8]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:7][CH2:6]1.C(N(CC)CC)C.[C:25]([C:27]1[CH:28]=[C:29]([N:33]=[C:34]=[O:35])[CH:30]=[CH:31][CH:32]=1)#[N:26]>CN(C=O)C.O>[C:25]([C:27]1[CH:28]=[C:29]([NH:33][C:34]([N:4]([CH2:3][CH2:2][OH:1])[CH:5]2[CH2:6][CH2:7][N:8]([CH2:11][C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH2:9][CH2:10]2)=[O:35])[CH:30]=[CH:31][CH:32]=1)#[N:26]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 27333153-IsocyanatobenzonitrileHCID 10681218HCID 10681218, compound

Product 1

HCID 18630643HCID 18630643, compoundYield 68.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred solution of 4-(2-hydroxyethyl)amino-1-benzylpiperidine (1.82 g), and triethylamine (0.789 g, 7.8 mmol) in DMF (50 mL) was added 3-cyanophenylisocyanate (1.12 g, 7.8 mmol). This mixture was heated at 60° C. for 18 under a N2 atmosphere. The reaction was diluted with water and extracted with ethyl acetate, dried with MgSO4, filtered and concentrated to give the desired product, N-(3-cyanophenyl)-N'-(2-hydroxyethyl)-N'-(1-benzylpiperidin-4-yl)urea (2.04 g, 5.3 mmol). LRMS (M+H)+ m/z 379.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialdried with MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-75eef0a45ece4c2abdb7f78e5f21bb53
Source dataset
uspto-grants-1999_07
Patent number
US05925635

Reaction notes

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