Carbon Disulfide → HCID 23294278, compound

HRID 1955234Notes

Reaction equation

HRID 1955234 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:22]=[CH:23][C:24]=1[NH2:25])[O:5][CH2:6][CH2:7][N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)[CH2:10][CH2:9]1.[OH-].[K+].[C:28](=S)=[S:29]>CCO.O>[Cl:21][C:18]1[CH:17]=[CH:16][C:15]([CH2:14][CH:11]2[CH2:12][CH2:13][N:8]([CH2:7][CH2:6][O:5][C:4]3[CH:22]=[CH:23][C:24]4=[N:25][C:28](=[S:29])[N:1]=[C:2]4[CH:3]=3)[CH2:9][CH2:10]2)=[CH:20][CH:19]=1

Participants

6

Reactant 3

HCID 6348Carbon DisulfideHCID 14797Potassium HydroxideHCID 23294384HCID 23294384, compound

Product 1

HCID 23294278HCID 23294278, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

From a mixture of 1-[2-(3,4-diaminophenoxy)ethyl]-4-(4-chlorobenzyl)piperidine (1.30 g, 3.67 mmol), KOH (240 mg, 4.28 mmol) and CS2 (250 μL, 4.16 mmol) in EtOH (5 mL) and water (0.8 mL) was obtained 1.28 g (88%) of the title compound as a foam solid. 1H NMR (CDCl3): 1.38-1.68 (m, 5H), 2.09-2.17 (m, 2H), 2.481 (d, 2H, J=6.5), 2.851 (t, 2H, J=4.5), 3.18-3.21 (m, 2H), 4.142 (t, 2H, J=4.5), 6.561 (bs, 1H), 6.596 (d, 1H, J=8.5), 6.936 (d, 1H, J=8.5), 7.036 (d, 2H, J=8), 7.029 (d, 2H, J=8). 1H NMR (DMSO-d6): 12.360 (s, 1H), 12.402 (s, 1H). The hydrochloride, mp. 291-3° C. Analysis, Calcd. for C21H25ClN3OS: C 57.53, H 5.75, N 9.58; Found: C 57.82, H 5.65, N 9.44.

Sources & evidence

ORD record
ord-3a96b60979ac45ea8515e370c6f99d06
Source dataset
uspto-grants-2000_09
Patent number
US06124323

Reaction notes

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