Dimethylformamide → HCID 22314795, compound

HRID 1634039Notes

Reaction equation

HRID 1634039 reaction equation
[ClH:1].[N:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]#[N:10])=[CH:4][CH:3]=1.[H-].[Na+].Br[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]Br.[NH4+].[Cl-].CN(C=[O:26])C>>[ClH:1].[NH:2]1[CH2:7][CH2:6][CH:5]([C:8]2([C:9]([NH2:10])=[O:26])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)[CH2:4][CH2:3]1

Participants

6

Reactant 5

HCID 6228DimethylformamideHCID 81001,5-DibromopentaneHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 123966084-Pyridylacetonitrile hydrochloride

Product 1

HCID 22314795HCID 22314795, compound

Conditions

Temperature
0 °C

Procedure

A mixture of 3 g of pyridin-4-ylacetonitrile hydrochloride in 50 ml of DMF is cooled to 0° C., 2.6 g of 60% sodium hydride in oil are added in small portions and the mixture is left stirring for 1 hour 30 minutes at RT. The reaction mixture is cooled on an ice bath, 2.7 ml of 1,5-dibromopentane are added dropwise and the mixture is left stirring for 48 hours at RT. The reaction mixture is poured over a saturated NH4Cl solution, extracted with ether, the organic phase washed three times with water, dried over MgSO4 and the solvent evaporated off under vacuum. The residue is chromatographed on H silica gel, eluting with DCM and then with the DCM/MeOH (98/2; v/v) mixture. 2.5 g of the expected product are obtained, m.p.=79° C.

Workup

  1. waitthe mixture is left
  2. temperatureThe reaction mixture is cooled on an ice bath
  3. waitthe mixture is left
  4. stirringstirring for 48 hours at RT
  5. extractionextracted with ether
  6. washthe organic phase washed three times with water
  7. dry with materialdried over MgSO4
  8. customthe solvent evaporated off under vacuum
  9. customThe residue is chromatographed on H silica gel
  10. washeluting with DCM

Sources & evidence

ORD record
ord-fb65194a29554e8baf33201987a57bbb
Source dataset
uspto-grants-2003_01
Patent number
US06506750B1

Reaction notes

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