Triphenylphosphine → HCID 58860678, compound

HRID 1350402Notes

Reaction equation

HRID 1350402 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][C:36]([C:39]([F:42])([F:41])[F:40])=[CH:35][CH:34]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[OH-].[Na+]>>[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][C:36]([C:39]([F:42])([F:41])[F:40])=[CH:35][CH:34]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 5

HCID 11776TriphenylphosphineHCID 14798Sodium HydroxideHCID 67993Benzene, 1-iodo-4-(trifluoromethyl)-HCID 789669-Borabicyclo(3.3.1)nonaneHCID 17759473(S)-1,4-dibenzyl-2-vinylpiperazine

Product 1

HCID 58860678HCID 58860678, compoundYield 37.1%

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-4-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, 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 3.34 g (37%) of the title compound: mass spectrum (ion spray): mp 71°–75°; m/z=439.2 (M+1); Analysis for C27H29F3N2: calcd: C, 73.95; H, 6.67; N, 6.39; found: C, 74.15; H, 6.72; N, 6.52.

Workup

  1. waitAfter 22 hrs
  2. customremove the THF under vacuum
  3. stirringstir the residue in 2N NaOH
  4. extractionextract with diethyl ether
  5. washWash the organic with 1N H2SO4
  6. extractionExtract the aqueous with diethyl ether and combine
  7. washwash (brine)
  8. dry with materialdry (sodium sulfate)
  9. customRecrystallize the residue in warm ethanol

Sources & evidence

ORD record
ord-8cbe5779492c42219a8e5c41c460ba93
Source dataset
uspto-grants-2007_05
Patent number
US07214673B2

Reaction notes

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