Hydrochloric Acid → HCID 13928816, compound

HRID 1608172Notes

Reaction equation

HRID 1608172 reaction equation
[F-:1].C([N+:6]([CH2:15][CH2:16][CH2:17][CH3:18])([CH2:11][CH2:12][CH2:13][CH3:14])CCCC)CCC.Cl.[C:20](#N)[CH3:21]>>[CH2:18]1[C:17]2[C:16](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:15]2([CH2:21][CH2:20][F:1])[NH:6][CH:11]1[C:12]1[C:13]2=[CH:14][CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 6342AcetonitrileHCID 2724141Tetrabutylammonium Fluoride

Product 1

HCID 13928816HCID 13928816, compoundYield 48%

Procedure

A 154 mg (0.31 mmol) sample of product from Step B was heated at 65° C. for 20 minutes in 3.0 mL of a 0.21M solution of tetra-n-butylammonium fluoride in acetonitrile, followed by treatment with 4.0 mL of 3.0M HCl at 65° C. for 15 minutes. The reaction mixture was washed with two portions of CHCl3, basified to pH 12 with 2.0M NaOH and extracted with two portions of CHCl3. The combined extracts were washed with water, dried over Na2SO4, and evaporated at reduced pressure to provide an oil which was chromatographed on silica gel using 98:2:0.2 CHCl3 --CH3OH--NH4OH and crystallized from hexanes to give 38 mg (48%) of the title compound as colorless crystals. 1H NMR,

Workup

  1. washThe reaction mixture was washed with two portions of CHCl3
  2. extractionextracted with two portions of CHCl3
  3. washThe combined extracts were washed with water
  4. dry with materialdried over Na2SO4
  5. customevaporated at reduced pressure
  6. customto provide an oil which
  7. customwas chromatographed on silica gel using 98:2:0.2 CHCl3
  8. customCH3OH--NH4OH and crystallized from hexanes

Sources & evidence

ORD record
ord-6308cf65d5f34f35b7ed9aed38afe87f
Source dataset
uspto-grants-1989_09
Patent number
US04870079

Reaction notes

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