Triphenylphosphine → HCID 58860671, compound

HRID 1350399Notes

Reaction equation

HRID 1350399 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]([Cl:39])=[CH:35][CH:34]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[OH-].[Na+]>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=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][C:36]([Cl:39])=[CH:35][CH:34]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 5

HCID 11776TriphenylphosphineHCID 125101-Chloro-4-iodobenzeneHCID 14798Sodium HydroxideHCID 789669-Borabicyclo(3.3.1)nonaneHCID 17759473(S)-1,4-dibenzyl-2-vinylpiperazine

Product 1

HCID 58860671HCID 58860671, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalyst

Procedure

Combine (S)-1,4-dibenzyl-2-vinyl-piperazine (5.0 g, 17.10 mmol) and 9-borabicyclo[3.3.1]nonane (136.8 ml, 68.39 mmol, 0.5 M in THF) and stir at ambient temperature. After 24 hrs, add 1-iodo-4-chloro-benzene (6.12 g, 25.65 mmol), triphenylphosphine (717.5 mg, 2.74 mmol), tetrakis(triphenylphosphine) palladium(0)(395.1 mg, 0.34 mmol), and 3N NaOH (14.0 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 4.76 g (69%) of the title compound: mp 87°–90°; mass spectrum (ion spray): m/z=405.4 (M+1); Analysis for C26H29ClN2: calcd: C, 77.11; H, 7.22; N, 6.92; found: C, 76.93; H, 7.06; N, 7.01.

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-1396d67339e8445bb221376d2a8151e6
Source dataset
uspto-grants-2007_05
Patent number
US07214673B2

Reaction notes

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