Water → HCID 178527893, compound

HRID 1589522Notes

Reaction equation

HRID 1589522 reaction equation
[N:1]1([CH2:7][C:8]2[CH:9]=[C:10]([CH:16]=[CH:17][CH:18]=2)[O:11][CH2:12][CH2:13][CH2:14][NH2:15])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[NH:19]1[CH:26]=[CH:25][C:23](=S)[NH:22][C:20]1=[S:21].O>N1C=CC=CC=1>[N:1]1([CH2:7][C:8]2[CH:9]=[C:10]([CH:16]=[CH:17][CH:18]=2)[O:11][CH2:12][CH2:13][CH2:14][NH:15][C:26]2[CH:25]=[CH:23][NH:22][C:20](=[S:21])[N:19]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 962WaterHCID 17124482,4-DithiouracilHCID 102205613-(3-(Piperidin-1-ylmethyl)phenoxy)propan-1-amine

Product 1

HCID 178527893HCID 178527893, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

3-(3-(Piperidinomethyl)phenoxy)propylamine (11.0 g) and dithiouracil (5.8 g) were refluxed in pyridine (100 ml; dried over potassium hydroxide) for approximately 72 hours. The solution was cooled and evaporated under reduced pressure to afford a residue. This residue was treated with water, evaporated under reduced pressure, and azeotroped thoroughly with n-propanol in an effort to remove pyridine. To the resultant residue was added further n-propanol to give the title compound as a solid which was collected by filtration and dried (13.88 g).

Workup

  1. temperatureThe solution was cooled
  2. customevaporated under reduced pressure
  3. customto afford a residue
  4. customevaporated under reduced pressure
  5. customazeotroped thoroughly with n-propanol in an effort
  6. customto remove pyridine
  7. additionTo the resultant residue was added further n-propanol

Sources & evidence

ORD record
ord-a3a4ba308fe54308baf3e66954ebe55a
Source dataset
uspto-grants-1986_02
Patent number
US04571398

Reaction notes

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