Dimethylformamide → n-(3-Cyanophenyl)-n'-((n-benzyl)piperidin-3-yl)cycloheptylurea

HRID 1059539Notes

Reaction equation

HRID 1059539 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([NH2:14])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:15]([C:17]1[CH:18]=[C:19](N=C=O)[CH:20]=C[CH:22]=1)#[N:16].[CH3:26][N:27]([CH3:30])[CH:28]=[O:29]>O>[C:15]([C:17]1[CH:22]=[C:26]([N:27]([CH:30]2[CH2:5][CH2:4][CH2:3][CH2:2][CH2:7][CH2:6]2)[C:28]([NH:14][CH:10]2[CH2:11][CH2:12][CH2:13][N:8]([CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH2:9]2)=[O:29])[CH:20]=[CH:19][CH:18]=1)#[N:16]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 4216941-Benzylpiperidin-3-amineHCID 27333153-Isocyanatobenzonitrile

Product 1

HCID 18630688n-(3-Cyanophenyl)-n'-((n-benzyl)piperidin-3-yl)cycloheptylurea

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4.3 g of N-benzyl 3-aminopiperidine (22.6 mmol) and 3-cyanophenyl isocyanate (3.58 g, 24.9 mmol) in dimethylformamide (100 mL) was stirred at ambient temperature for 18 h. The reaction was diluted with water (500 mL) and extracted with ethyl acetate (3×150 mL). The organic solution was washed with water (5×100 mL), dried and evaporated. This material was purified further by flash chromatography on silica gel using a gradient of 1:1 to 3:1 ethyl acetate:hexane. There was obtained 3.18 g of the pure urea (9.52 mmol); LRMS (M+H)+ m/z=335.

Workup

  1. extractionextracted with ethyl acetate (3×150 mL)
  2. washThe organic solution was washed with water (5×100 mL)
  3. customdried
  4. customevaporated
  5. customThis material was purified further by flash chromatography on silica gel using a gradient of 1:1 to 3:1 ethyl acetate

Sources & evidence

ORD record
ord-765b9fa9ce3141c39857618df1030bc1
Source dataset
uspto-grants-2003_02
Patent number
US06521614B1

Reaction notes

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