Carbon Disulfide → HCID 23294344, compound

HRID 1955230Notes

Reaction equation

HRID 1955230 reaction equation
[CH2:1]([CH:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][O:16][C:17]2[CH:22]=[CH:21][C:20]([NH2:23])=[C:19]([NH2:24])[CH:18]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+].[C:27](=S)=[S:28]>CCO.O>[CH2:1]([CH:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][O:16][C:17]2[CH:22]=[CH:21][C:20]3=[N:23][C:27](=[S:28])[N:24]=[C:19]3[CH:18]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 6348Carbon DisulfideHCID 14797Potassium HydroxideHCID 23294226HCID 23294226, compound

Product 1

HCID 23294344HCID 23294344, compoundYield 68.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of 4-benzyl-1-[(3,4-diaminophenoxy)ethyl]piperidine (326 mg, 1.0 mmol), KOH (66 mg, 1.1 mmol) and CS2 (66 μL, 1.1 mmol) in 95% EtOH (1.5 mL) and H2O (0.2 mL) was refluxed for 3 h, then evaporated, and the residue was purified by chromatography over silica gel (CHCl3 --MeOH, 4:1) to give 250 mg (68%) of the title compound as a foam solid. 1H NMR (DMSO-d6): 1.40-1.48 (m, 2H), 1.54-1.61 (m, 1H), 1.67-1.71 (m, 2H), 2.09-2.18 (m, 2H), 2.517 (d, 2H, J=6), 2.841 (t, 2H, J=5), 3.17-3.20 (m,2H), 4.139 (t, 2H, J=5), 6.551 (d, 1H, J=2), 6.605 (dd, 1H, J=8.5; 2), 6.950 (d, 1H, J=8.5), 7.11-7.28 (m, 5H). The hydrochloride, mp. 273-5° C. Analysis, Calcd. for C21H26ClN3OS: C 62.44, H 6.49, N 10.40; Found: C 62.28, H 6.42, N 10.21.

Workup

  1. temperaturewas refluxed for 3 h
  2. customevaporated
  3. customthe residue was purified by chromatography over silica gel (CHCl3 --MeOH, 4:1)

Sources & evidence

ORD record
ord-1891b99414b24475913b7335e5a295bb
Source dataset
uspto-grants-2000_09
Patent number
US06124323

Reaction notes

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