Hydrochloric Acid → HCID 21216804, compound

HRID 1586440Notes

Reaction equation

HRID 1586440 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH:10]([C:13]2[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=2)[C:11]#[N:12])=[CH:4][CH:3]=1.[NH2-].[Na+].[CH2:21](Br)[CH:22]=[CH2:23].Cl>O1CCCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][C:10]([CH2:23][CH:22]=[CH2:21])([C:13]2[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=2)[C:11]#[N:12])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7841Allyl bromideHCID 24533Sodium amideHCID 54351091HCID 54351091, compound

Product 1

HCID 21216804HCID 21216804, compoundYield 79.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of α-[2-(4-fluorophenyl)ethyl]-3-pyridineacetonitrile (4 g) in tetrahydrofuran (30 ml) was added dropwise, under nitrogen atmosphere, to a stirred suspension of sodium amide (0.8 g) at 0° C. After complete addition (~20 minutes) the resultant mixture was stirred at 0° C. for 1 hour followed by 1 hour at room temperature. The mixture was then cooled to -40° C. and treated with dropwise addition of a solution of allyl bromide (2 g) in tetrahydrofuran (30 ml) to produce a reaction mixture. The reaction mixture was allowed to warm up to room temperature overnight, then neutralized with 10% hydrochloric acid and worked up by extraction with methylene chloride to produce a crude reaction product. The crude reaction product was then chromatographed on a silica gel column and eluted with 25% ethyl acetate in hexanes to give 3.7 g of 4-fluoro-α-(2-propenyl)-α-(3-pyridinyl)benzene-butanenitrile. The structure was confirmed by NMR spectroscopy.

Workup

  1. waitfollowed by 1 hour at room temperature
  2. temperatureThe mixture was then cooled to -40° C.
  3. customto produce a reaction mixture
  4. temperatureto warm up to room temperature overnight
  5. extractionworked up by extraction with methylene chloride
  6. customto produce a crude
  7. customreaction product
  8. customThe crude reaction product
  9. customwas then chromatographed on a silica gel column
  10. washeluted with 25% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-0ba170df7ea04398b234a8f0b9d0ed2c
Source dataset
uspto-grants-1999_08
Patent number
US05945436

Reaction notes

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