Water → HCID 85876305, compound

HRID 2110032Notes

Reaction equation

HRID 2110032 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][N:10]2[CH2:15][CH2:14][CH:13]([CH2:16][NH:17][C:18](=[S:37])[NH:19]C(OCC3C4C=CC=CC=4C4C3=CC=CC=4)=O)[CH2:12][CH2:11]2)[CH:5]=[CH:6][C:7]=1[Cl:8].N1CCCCC1.O>CN(C=O)C>[NH2:19][C:18]([NH:17][CH2:16][CH:13]1[CH2:14][CH2:15][N:10]([CH2:9][C:4]2[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=2)[CH2:11][CH2:12]1)=[S:37]

Participants

5

Reactant 3

HCID 962WaterHCID 8082PiperidineHCID 87680503HCID 87680503, compound

Product 1

HCID 85876305HCID 85876305, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

After dissolving N-{[({1-[(3,4-dichlorophenyl)methyl](4-piperidyl)}methyl)amino]thioxomethyl}(fluoren-9-ylmethoxy)carboxamide (553 mg, 1 mmol) in DMF (4 ml), piperidine (0.989 ml, 10 mmol) was added and the mixture was stirred at room temperature overnight. Upon completion of the reaction, water (20 ml) was added and extraction was performed with ethyl acetate (20 ml×3 times). The extracted organic layer was washed with water (100 ml×2 times) and then with saturated brine, dried over anhydrous sodium sulfate, and then filtered and concentrated. Purification was performed by silica gel column chromatography (ethyl acetate/methanol=1/0→4/1) to obtain amino[({1-[(3,4-dichlorophenyl)methyl](4-piperidyl)}methyl)amino]methane-1-thione. The compound was identified by LC-MS.

Workup

  1. additionwas added
  2. additionwas added
  3. extractionextraction
  4. washThe extracted organic layer was washed with water (100 ml×2 times)
  5. dry with materialwith saturated brine, dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification

Sources & evidence

ORD record
ord-640f900a4fe34870a830255e4619f40f
Source dataset
uspto-grants-2009_04
Patent number
US07517875B2

Reaction notes

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