Diethylamine → HCID 178464159, compound

HRID 1876244Notes

Reaction equation

HRID 1876244 reaction equation
[C:1]([C:3]1[N:7]([CH3:8])[C:6]([C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[NH:14][C:13](=[N:18][C:19]#[N:20])[C:12]23[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)=[CH:5][CH:4]=1)#[N:2].C(NCC)C>C1COCC1>[CH2:6]([NH:7][CH2:3][CH3:1])[CH3:5].[C:1]([C:3]1[N:7]([CH3:8])[C:6]([C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[NH:14][C:13](=[N:18][C:19]#[N:20])[C:12]23[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)=[CH:5][CH:4]=1)#[N:2]

Participants

4

Reactant 2

HCID 8021DiethylamineHCID 178480854HCID 178480854, compound

Product 1

HCID 178464159HCID 178464159, compoundYield 184.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5′-(5-Cyano-1-methyl-1H-pyrrol-2-yl)spiro[cyclohexane-1,3′-[3H]indol]-2′-ylidenecyanamide (16 g) in THF (100 mL) was treated with diethylamine (37 g) and refluxed until a solution was obtained. Upon cooling to ambient temperature, a white precipitate was formed. The solution was filtered, the precipitate washed with THF and dried to give 18.0 g (90% yield) of the diethylamine salt/complex. 1H NMR (DMSO-d6, ppm): 7.58, 7.21, 7.05, 7.00, 6.5-6 (br), 6.27, 3.71, 2.80 (q), 1.9-1.7, 1.5-1.4, and 1.10 (t).

Workup

  1. temperaturerefluxed until a solution
  2. customwas obtained
  3. customa white precipitate was formed
  4. filtrationThe solution was filtered
  5. washthe precipitate washed with THF
  6. customdried

Sources & evidence

ORD record
ord-7162ffcfd2e248a7aea9b19bc54cf013
Source dataset
uspto-grants-2012_11
Patent number
US08309594B2

Reaction notes

Loading…