Triphenylphosphine → HCID 58860682, compound

HRID 1350403Notes

Reaction equation

HRID 1350403 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:10][C@@H:9]1[CH:21]=[CH2:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C12BC(CCC1)CCC2.I[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=1[C:39]([F:42])([F:41])[F:40].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[OH-].[Na+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:10][C@@H:9]1[CH2:21][CH2:22][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=1[C:39]([F:42])([F:41])[F:40])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 5

HCID 11776TriphenylphosphineHCID 14798Sodium HydroxideHCID 67957Benzene, 1-iodo-2-(trifluoromethyl)-HCID 789669-Borabicyclo(3.3.1)nonaneHCID 17759473(S)-1,4-dibenzyl-2-vinylpiperazine

Product 1

HCID 58860682HCID 58860682, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

Combine (S)-1,4-dibenzyl-2-vinyl-piperazine (6.0 g, 20.52 mmol) and 9-borabicyclo[3.3.1]nonane (164.1 ml, 82.07 mmol, 0.5 M in THF) and stir at ambient temperature. After 24 hrs, add 1-iodo-2-trifluoromethyl-benzene (8.37 g, 30.78 mmol), triphenylphosphine (861.0 mg, 3.28 mmol), tetrakis(triphenylphosphine)palladium(0)(474.1 mg, 0.41 mmol), and 3N NaOH (16.8 ml) and stir at 60°. After 22 hrs, remove the THF under vacuum and dissolve the residue in ethyl acetate. Wash the organic layer with 1N NaOH then combine, wash (brine), dry (sodium sulfate), and reduce the extracts to residue. Purify the residue using ethyl acetate/hexanes (5:95) and reduce the appropriate fractions to residue. Stir the residue in 2N NaOH, and extract with diethyl ether. Wash the organic with 1N H2SO4 then adjust the aqueous to pH 14. Extract the aqueous with diethyl ether and combine, wash (brine), dry (sodium sulfate), and reduce the extracts to residue. Recrystallize the residue in warm ethanol to give 2.67 g (30%) of the title compound: mass spectrum (ion spray): mp 77°–82°; m/z=439.2 (M+1); Analysis for C27H29F3N2: calcd: C, 73.95; H, 6.67; N, 6.39; found: C, 74.11; H, 6.68; N, 6.50.

Workup

  1. waitAfter 22 hrs
  2. customremove the THF under vacuum
  3. dissolutiondissolve the residue in ethyl acetate
  4. washWash the organic layer with 1N NaOH
  5. washwash (brine)
  6. dry with materialdry (sodium sulfate)
  7. customPurify the residue
  8. stirringStir the residue in 2N NaOH
  9. extractionextract with diethyl ether
  10. washWash the organic with 1N H2SO4
  11. extractionExtract the aqueous with diethyl ether and combine
  12. washwash (brine)
  13. dry with materialdry (sodium sulfate)
  14. customRecrystallize the residue in warm ethanol

Sources & evidence

ORD record
ord-2abc12b40bba4cdf8edf088e54d41fe4
Source dataset
uspto-grants-2007_05
Patent number
US07214673B2

Reaction notes

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