Triphenylphosphine → HCID 69486910, compound

HRID 1350384Notes

Reaction equation

HRID 1350384 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[O:39][CH3:40].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][CH:36]=[CH:35][C:34]=1[O:39][CH3:40])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 5

HCID 11776TriphenylphosphineHCID 14798Sodium HydroxideHCID 68257o-IodoanisoleHCID 789669-Borabicyclo(3.3.1)nonaneHCID 17759473(S)-1,4-dibenzyl-2-vinylpiperazine

Product 1

HCID 69486910HCID 69486910, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalyst

Conditions

Temperature
60 °C

Procedure

Combine (S)-1,4-dibenzyl-2-vinyl-piperazine (2.5 g, 8.55 mmol) and 9-borabicyclo[3.3.1]nonane (68.4 mL, 34.20 mmol, 0.5 M in THF) and stir at ambient temperature. After 24 hours, add 1-iodo-2-methoxy-benzene (3.0 g, 12.82 mmol), triphenylphosphine (358.8 mg, 1.37 mmol), tetrakis(triphenylphosphine) palladium(0) (197.5 mg, 0.17 mmol), and 3N NaOH (7.0 mL) and stir at 60° C. After 22 hours, 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. Purify the residue on silica gel using ethyl acetate/hexanes (5:95) to give (2.21 g, 65%) of the title compound: mp 58–61 C°; mass spectrum (ion spray): m/z=401.3 (M+1); Analysis for C27H32N2O: calcd: C, 80.96; H, 8.05; N, 6.99; found: C, 81.08; H, 7.99; N, 7.10.

Workup

  1. waitAfter 22 hours
  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. customPurify the residue on silica gel

Sources & evidence

ORD record
ord-08471d1baee542f4aa88fc6b1d1ac6ee
Source dataset
uspto-grants-2007_05
Patent number
US07214673B2

Reaction notes

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