Dimethylformamide → HCID 86735877, compound

HRID 2419023Notes

Reaction equation

HRID 2419023 reaction equation
[C:1]1([CH:7]2[CH2:12][NH:11][CH2:10][C:9]3[S:13][CH:14]=[CH:15][C:8]2=3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([CH:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)#N.C(=O)([O-])[O-].[K+].[K+].[CH3:32][N:33](C)C=O>>[C:32]([C:15]1[C:8]2[CH:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[CH2:12][NH:11][CH2:10][C:9]=2[S:13][C:14]=1[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)#[N:33]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 22044Bromobenzyl CyanideHCID 127369914-Phenyl-4,5,6,7-tetrahydrothieno[2,3-c]pyridine

Product 1

HCID 86735877HCID 86735877, compoundYield 67%

Procedure

A mixture of 4-phenyl-4,5,6,7-tetrahydro-thieno[2,3-c]pyridine (6 g; 0.028 mole) (Example 3), o.cyanobenzyl bromide (5.9 g; 0.03 mole) and solid potassium carbonate (5.8 g; 0.042 mole) in dimethylformamide (100 ml) is heated at 70° C during 2 hours. After cooling, the precipitate is filtered and the solvent is evaporated off under reduced pressure. The residue is taken up into water and extracted with ether. The organic extracts are washed with water, dried over sodium sulfate, filtered through a silica bed and evaporated to dryness. The residue is recrystallized from cyclohexane: M.p. = 124° C (Yield: 67%).

Workup

  1. temperatureAfter cooling
  2. filtrationthe precipitate is filtered
  3. customthe solvent is evaporated off under reduced pressure
  4. extractionextracted with ether
  5. washThe organic extracts are washed with water
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered through a silica bed
  8. customevaporated to dryness
  9. customThe residue is recrystallized from cyclohexane

Sources & evidence

ORD record
ord-99b2fb96c3f74b878331850c2a9777b8
Source dataset
uspto-grants-1978_08
Patent number
US04104390

Reaction notes

Loading…