Water → HCID 178498411, compound

HRID 611485Notes

Reaction equation

HRID 611485 reaction equation
[Na].[C:2]([NH:4][C:5](=[N:7][CH2:8][CH2:9][CH2:10][N:11]1[CH2:16][CH2:15][CH:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:13][CH2:12]1)S)#[N:3].[CH3:23][C:24]1[NH:25][C:26]([CH3:46])=[C:27]([C:42]([O:44][CH3:45])=[O:43])[CH:28]([C:34]2[CH:39]=[CH:38][CH:37]=[C:36]([NH:40][CH3:41])[CH:35]=2)[C:29]=1[C:30]([O:32][CH3:33])=[O:31].O>C1COCC1.Cl[Hg]Cl>[C:2]([N:4]=[C:5]([N:40]([CH3:41])[C:36]1[CH:35]=[C:34]([CH:28]2[C:29]([C:30]([O:32][CH3:33])=[O:31])=[C:24]([CH3:23])[NH:25][C:26]([CH3:46])=[C:27]2[C:42]([O:44][CH3:45])=[O:43])[CH:39]=[CH:38][CH:37]=1)[NH:7][CH2:8][CH2:9][CH2:10][N:11]1[CH2:16][CH2:15][CH:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:13][CH2:12]1)#[N:3]

Participants

6

Reactant 3

HCID 962WaterHCID 15886879HCID 15886879, compoundHCID 178512429HCID 178512429, compound

Product 1

HCID 178498411HCID 178498411, compoundYield 4.5%

Reagents, catalysts & solvents 2

HCID 24085Mercuric ChlorideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-cyano-N'-[3-(4-phenyl-1-piperidinyl)propyl]isothiourea sodium salt (IX) (115 mg, 0.35 mmol) and the aniline intermediate (XIV) from Example 12 (115 mg, 0.35 mmol) in THF (7 mL) at 0° C. was added HgCl2 (95 mg, 0.35 mmol). The reaction mixture was then refluxed for 3 h. After cooling to room temperature, H2O (1 mL) was added, and the mixture was stirred for 30 min. A gray precipitate was collected by filtration, and rinsed with CH2Cl2, the organic extract was dried (Na2SO4), and the solvent was removed in vacuo. The residue was subjected twice to flash chromatography (silica gel, MeOH:CH2Cl2, 4:96) to afford the compound as a white solid (15 mg, 4.5%). mp 85-90° C.; MS (ESI) m/z 599 (MH+); 1H NMR (CDCl3) δ 7.30 (m, 8 h), 6.98 (d, 1H, J=7.8 Hz), 6.91 (s, 1H), 5.29 (br s, 1H), 5.09 (s, 1 H), 3.67 (s, 6H), 3.63 (m, 2H), 3.47 (m, 2H), 3.37 (s, 3H), 3.00 (m, 2H), 2.73 (m, 4H), 2.45 (s, 6H), 2.38 (m, 1H), 2.26 (m, 2H), 2.03 (m, 2H); 13C NMR (CDCl3) δ 168.2, 150.4, 146.8, 130.6, 129.0, 128.0, 127.4, 127.0, 124.9, 124.1, 117.3, 102.3, 54.1, 51.4, 51.3, 40.8, 40.3, 39.9, 38.9, 30.4, 25.4, 19.3. HRMS (FAB) Calcd. for C34H43N6O4 (MH+): m/z 599.3346. Found: 599.3362.

Workup

  1. customat 0° C.
  2. temperatureThe reaction mixture was then refluxed for 3 h
  3. filtrationA gray precipitate was collected by filtration
  4. washrinsed with CH2Cl2
  5. extractionthe organic extract
  6. dry with materialwas dried (Na2SO4)
  7. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-a874bac620cd4565bcde4c56be3aaf4e
Source dataset
uspto-grants-1999_12
Patent number
US06001836

Reaction notes

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