Dimethylformamide → HCID 18630643, compound

HRID 1059519Notes

Reaction equation

HRID 1059519 reaction equation
OCC[CH:4]1[CH2:9][CH2:8][N:7]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:6](N)[CH2:5]1.[CH2:18]([N:20](CC)CC)[CH3:19].[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:40])C>O>[C:25]([C:27]1[CH:28]=[C:29]([NH:33][C:34]([N:20]([CH2:18][CH2:19][OH:40])[CH:4]2[CH2:5][CH2:6][N:7]([CH2:10][C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH2:8][CH2:9]2)=[O:35])[CH:30]=[CH:31][CH:32]=1)#[N:26]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 27333153-IsocyanatobenzonitrileHCID 69831822HCID 69831822, compound

Product 1

HCID 18630643HCID 18630643, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

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-1a2d670c5c0c4c9cbda22dd4a09df89d
Source dataset
uspto-grants-2003_02
Patent number
US06521614B1

Reaction notes

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