Phenyl Isothiocyanate → N-Phenyl-7-[1-(pyridin-4-yl)piperidin-4-ylmethoxy]-1,2,3,4-tetrahydroisoquinoline-2-carbothioamide

HRID 412520Notes

Reaction equation

HRID 412520 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([N:7]2[CH2:12][CH2:11][CH:10]([CH2:13][O:14][C:15]3[CH:24]=[C:23]4[C:18]([CH2:19][CH2:20][NH:21][CH2:22]4)=[CH:17][CH:16]=3)[CH2:9][CH2:8]2)=[CH:3][CH:2]=1.[C:25]1([N:31]=[C:32]=[S:33])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>C(Cl)Cl>[C:25]1([NH:31][C:32]([N:21]2[CH2:20][CH2:19][C:18]3[C:23](=[CH:24][C:15]([O:14][CH2:13][CH:10]4[CH2:9][CH2:8][N:7]([C:4]5[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=5)[CH2:12][CH2:11]4)=[CH:16][CH:17]=3)[CH2:22]2)=[S:33])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

4

Reactant 2

HCID 7673Phenyl IsothiocyanateHCID 113247627-[1-(Pyridin-4-yl)piperidin-4-ylmethoxy]-1,2,3,4-tetrahydroisoquinoline

Product 1

HCID 18536507N-Phenyl-7-[1-(pyridin-4-yl)piperidin-4-ylmethoxy]-1,2,3,4-tetrahydroisoquinoline-2-carbothioamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 7-[1-(pyridin-4-yl)piperidin-4-ylmethoxy]-1,2,3,4-tetrahydroisoquinoline (30 mg) in methylene chloride (0.5 ml) was added phenyl isothiocyanate (0.012 ml), and the mixture was stirred at room temperature for 1 hour. After completion of the reaction, the solvent was evaporated and the obtained residue was purified by silica gel column chromatography (chloroform:methanol=100:1, 1% triethylamine) and dried under reduced pressure to give the title compound (40 mg).

Workup

  1. customAfter completion of the reaction
  2. customthe solvent was evaporated
  3. customthe obtained residue was purified by silica gel column chromatography (chloroform:methanol=100:1, 1% triethylamine)
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-1a5927dae31442359c9badf7fc10f8cf
Source dataset
uspto-grants-2003_05
Patent number
US06562828B1

Reaction notes

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