Thiophenol → N-(2-pyridinylmethyl)-N'-(4-methoxy-5,6,7,8-tetrahydro-8-quinolinyl)-1,4-benzenedimethanamine

HRID 983620Notes

Reaction equation

HRID 983620 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][N:8](S(C1C=CC=CC=1[N+]([O-])=O)(=O)=O)[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][NH:17][CH:18]2[C:27]3[N:26]=[CH:25][CH:24]=[C:23]([O:28][CH3:29])[C:22]=3[CH2:21][CH2:20][CH2:19]2)=[CH:12][CH:11]=1.C1(S)C=CC=CC=1.C([O-])([O-])=O.[K+].[K+]>CC#N>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][NH:8][CH2:9][C:10]1[CH:11]=[CH:12][C:13]([CH2:16][NH:17][CH:18]2[C:27]3[N:26]=[CH:25][CH:24]=[C:23]([O:28][CH3:29])[C:22]=3[CH2:21][CH2:20][CH2:19]2)=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 7969ThiophenolHCID 11430Potassium CarbonateHCID 22018772N-(2-pyridinylmethyl)-N-(2-nitrobenzenesulfonyl)-N'-(4-methoxy-5,6,7,8-tetrahydro-8-quinolinyl)-1,4-benzenedimethanamine

Product 1

HCID 22018571N-(2-pyridinylmethyl)-N'-(4-methoxy-5,6,7,8-tetrahydro-8-quinolinyl)-1,4-benzenedimethanamineYield 82%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

N-(2-pyridinylmethyl)-N-(2-nitrobenzenesulfonyl)-N′-(4-methoxy-5,6,7,8-tetrahydro-8-quinolinyl)-1,4-benzenedimethanamine (0.269 g, 0.50 mmol) was treated with thiophenol (0.35 mL, 3.41 mmol) and K2CO3 (0.757 g, 5.48 mmol) in CH3CN (10 mL). Purification of the crude material by radial chromatography on silica gel (2 mm plate, 20:1:1 CH2Cl2-CH3OH NH4OH) provided 0.158 g (82%) of the title compound as a yellow oil. 1H NMR (CDCl3) □1.61-1.80 (m, 2H), 1.98-2.17 (m, 2H), 2.56-2.70 (m, 2H), 3.79-3.83 (m, 6H), 3.88-3.98 (m, 4H), 6.60 (d, 1H, J=5.7 Hz), 7.15 (dd, 1H, J=5.1, 6.9 Hz), 7.23-7.41 (m, 5H) 7.63 (ddd, 1H, J=7.8, 7.8, 1.8 Hz), 8.30 (d, 1H, J=5.7 Hz); 8.55 (d, 1H, J=3.9 Hz);

Workup

  1. customPurification of the crude material by radial chromatography on silica gel (2 mm plate, 20:1:1 CH2Cl2-CH3OH NH4OH)

Sources & evidence

ORD record
ord-7d4652eb666e4dab974ad7824ae7f583
Source dataset
uspto-grants-2005_03
Patent number
US06864265B2

Reaction notes

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