Acetonitrile → HCID 70258191, compound

HRID 377240Notes

Reaction equation

HRID 377240 reaction equation
[CH2:1]([N:8]1[C:12]2[CH:13]=[C:14]([O:17][CH2:18][CH2:19]Cl)[CH:15]=[CH:16][C:11]=2[N:10]=[C:9]1[C:21]1[CH:26]=[C:25]([O:27][CH3:28])[C:24]([O:29][CH3:30])=[C:23]([O:31][CH3:32])[CH:22]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:33]1[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]1.C([N:42]([CH2:46][CH3:47])[CH:43]([CH3:45])C)(C)C.[C:48](#N)C>[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:1]([N:8]1[C:12]2[CH:13]=[C:14]([O:17][CH2:18][CH2:19][N:33]3[CH2:38][CH2:37][CH:36]([N:42]4[CH2:43][CH2:45][CH2:48][CH2:47][CH2:46]4)[CH2:35][CH2:34]3)[CH:15]=[CH:16][C:11]=2[N:10]=[C:9]1[C:21]1[CH:26]=[C:25]([O:27][CH3:28])[C:24]([O:29][CH3:30])=[C:23]([O:31][CH3:32])[CH:22]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 8082PiperidineHCID 81531DiisopropylethylamineHCID 19353940HCID 19353940, compound

Product 1

HCID 70258191HCID 70258191, compound

Reagents, catalysts & solvents 1

HCID 67553Tetrabutylammonium IodideCatalyst

Procedure

The title compound was prepared by reacting the compound of Example 76, supra, (0.45 g, 1.0 mmol) with 4-piperdin-1-yl)piperidine (2.0 g, 11.9 mmol) in the presence of the base N,N-diisopropylethylamine, tetra-n-butylammonium iodide and acetonitrile at 80° C. After incubating overnight at 80° C. the reaction was washed with water (2×500 ml), followed by a wash with a saturated sodium chloride solution (1×500 ml). The organic phase was then dried over potassium carbonate and the solvents were removed in vacuo to yield a light brown oil. The desired product was purified by chromatography and triturated with diethyl ether to yield a light brown powder, which was removed by filtration and washed with diethyl ether to yield the purified title compound. MS 584, 585, NMR, IR, mp 143° C.

Workup

  1. customat 80° C
  2. washthe reaction was washed with water (2×500 ml)
  3. washa wash with a saturated sodium chloride solution (1×500 ml)
  4. dry with materialThe organic phase was then dried over potassium carbonate
  5. customthe solvents were removed in vacuo
  6. customto yield a light brown oil
  7. customThe desired product was purified by chromatography
  8. customtriturated with diethyl ether
  9. customto yield a light brown powder, which
  10. customwas removed by filtration
  11. washwashed with diethyl ether
  12. customto yield the
  13. custompurified title compound

Sources & evidence

ORD record
ord-759867f4c9bf4db68d219aa4ea416e39
Source dataset
uspto-grants-2000_02
Patent number
US06025379

Reaction notes

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