Fmoc isothiocyanate → HCID 87680503, compound

HRID 2110031Notes

Reaction equation

HRID 2110031 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][N:10]2[CH2:15][CH2:14][CH:13]([CH2:16][NH2:17])[CH2:12][CH2:11]2)[CH:5]=[CH:6][C:7]=1[Cl:8].[CH:18]1[C:30]2[CH:29]([CH2:31][O:32][C:33]([N:35]=[C:36]=[S:37])=[O:34])[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[C:22]=2[CH:21]=[CH:20][CH:19]=1>O1CCCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][N:10]2[CH2:11][CH2:12][CH:13]([CH2:16][NH:17][C:36](=[S:37])[NH:35][C:33]([O:32][CH2:31][CH:29]3[C:28]4[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=4[C:22]4[C:30]3=[CH:18][CH:19]=[CH:20][CH:21]=4)=[O:34])[CH2:14][CH2:15]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

4

Reactant 2

HCID 4154759Fmoc isothiocyanateHCID 43130924HCID 43130924, compound

Product 1

HCID 87680503HCID 87680503, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

After dissolving {1-[(3,4-dichlorophenyl)methyl]-4-piperidyl}methylamine (1325 mg, 4.84 mmol) in tetrahydrofuran (20 ml), FmocNCS (9-fluorenylmethoxycarbonyl isothiocyanate) (1498 mg, 5.32 mmol) was added, and the mixture was stirred at room temperature overnight. After completion of the reaction, the reaction mixture was concentrated and purified by silica gel column chromatography (hexane/ethyl acetate=85/15) to obtain N-{[({1-[(3,4-dichlorophenyl)methyl](4-piperidyl)}methyl)amino]thioxomethyl}(fluoren-9-ylmethoxy)carboxamide. The compound was identified by LC-MS.

Workup

  1. additionwas added
  2. customAfter completion of the reaction
  3. concentrationthe reaction mixture was concentrated
  4. custompurified by silica gel column chromatography (hexane/ethyl acetate=85/15)

Sources & evidence

ORD record
ord-a11b89d55a14408cba0eb7b55c1b6482
Source dataset
uspto-grants-2009_04
Patent number
US07517875B2

Reaction notes

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