1,1'-Thiocarbonyldi-2(1H)-pyridone → HCID 59286676, compound

HRID 1876030Notes

Reaction equation

HRID 1876030 reaction equation
[C:1](N1C=CC=CC1=O)(N1C=CC=CC1=O)=[S:2].[CH:17]1[C:26]2[CH2:25][CH2:24][CH2:23][CH2:22][C:21]=2[CH:20]=[C:19]([NH2:27])[N:18]=1>ClCCl.C(OCC)(=O)C.CCCCCC>[N:27]([C:19]1[N:18]=[CH:17][C:26]2[CH2:25][CH2:24][CH2:23][CH2:22][C:21]=2[CH:20]=1)=[C:1]=[S:2]

Participants

5

Reactant 2

HCID 8531621,1'-Thiocarbonyldi-2(1H)-pyridoneHCID 133023975,6,7,8-Tetrahydroisoquinolin-3-amine

Product 1

HCID 59286676HCID 59286676, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

To a stirring solution of 1,1′-thiocarbonyldipyridin-2(1H)-one (222 mg, 0.956 mmol) in dchloromethane (5 mL) was added a solution of 5,6,7,8-tetrahydroisoquinolin-3-amine (139 mg, 0.938 mmol) in dichloromethane (1.5 mL) and the resulting solution was stirred at room temperature overnight. The reaction mixture was applied directly to a Biotage column in 20-25% ethyl acetate/hexane, collecting the first major peak. Yield 141.8 mg (79%) 3-iothiocyanato-5,6,7,8-tetrahydroisoquinoline. NMR 1H NMR (500 MHz, CHLOROFORM-d) δ ppm 8.10 (1H, s), 6.84 (1H, s), 2.74 (4H, t, J=6.3 Hz), 1.81 (4H, dd, J=4.0, 2.7 Hz).

Workup

  1. customcollecting the first major peak

Sources & evidence

ORD record
ord-998a3947339e4518beb77a9dadca41e3
Source dataset
uspto-grants-2012_11
Patent number
US08309577B2

Reaction notes

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