Triethylamine → 4-[5-(spiro[3H-indole-3,4'-piperidine]-2(1H)-on-1'-ylmethyl)imidazol-1-ylmethyl]benzonitrile

HRID 565610Notes

Reaction equation

HRID 565610 reaction equation
[NH:1]1[CH2:6][CH2:5][C:4]2([C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[NH:8][C:7]2=[O:15])[CH2:3][CH2:2]1.Cl.[C:17]([C:19]1[CH:32]=[CH:31][C:22]([CH2:23][N:24]2[C:28]([CH2:29]Cl)=[CH:27][N:26]=[CH:25]2)=[CH:21][CH:20]=1)#[N:18].C(N(CC)CC)C>C(#N)C.C(OCC)(=O)C>[N:1]1([CH2:29][C:28]2[N:24]([CH2:23][C:22]3[CH:31]=[CH:32][C:19]([C:17]#[N:18])=[CH:20][CH:21]=3)[CH:25]=[N:26][CH:27]=2)[CH2:6][CH2:5][C:4]2([C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[NH:8][C:7]2=[O:15])[CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 97953574-((5-(Chloromethyl)-1H-imidazol-1-yl)methyl)benzonitrile hydrochlorideHCID 18435788Spiro(indole-3,4'-piperidin)-2(1H)-one

Product 1

HCID 98221494-[5-(spiro[3H-indole-3,4'-piperidine]-2(1H)-on-1'-ylmethyl)imidazol-1-ylmethyl]benzonitrile

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of spiro[3H-indole-3,4′-piperidin]-2(1H)-one, as described above in Step B, (110 mg, 0.54 mmol), 1-(4-cyanobenzyl)-5-chloromethylimidazole hydrochloride salt, as described in Example 1, Alternate Step A, (134 mg, 0.50 mmol), and triethylamine (0.21 mL, 1.5 mmol) in anhydrous acetonitrile (1.5 mL) was stirred at room temp. for 15 hours. The resulting mixture was diluted with ethyl acetate and the solution washed with sat'd aqueous sodium carbonate, dried (anhyd. sodium sulfate), filtered and concentrated under vacuum. The resulting residue was triturated with ethyl acetate to give a white solid which was collected to afford the title compound as a crystalline freebase, mp: 245-247° C.

Workup

  1. washthe solution washed with sat'd aqueous sodium carbonate
  2. dry with materialdried (anhyd. sodium sulfate)
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum
  5. customThe resulting residue was triturated with ethyl acetate
  6. customto give a white solid which
  7. customwas collected

Sources & evidence

ORD record
ord-570f0fbf696d45b599f35361f35be06f
Source dataset
uspto-grants-2001_01
Patent number
US06172076B2

Reaction notes

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