Triphenylphosphine → (S)-1,4-Dibenzyl-2-(2-pridin-4-yl-ethyl)-piperazine

HRID 1350362Notes

Reaction equation

HRID 1350362 reaction equation
C12BC(CCC1)CCC2.[CH2:10]([N:17]1[CH2:22][CH2:21][N:20]([CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:19][C@@H:18]1[CH:30]=[CH2:31])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.Cl.Br[C:53]1[CH:58]=[CH:57][N:56]=[CH:55][CH:54]=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>[CH2:10]([N:17]1[CH2:22][CH2:21][N:20]([CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:19][C@@H:18]1[CH2:30][CH2:31][C:53]1[CH:58]=[CH:57][N:56]=[CH:55][CH:54]=1)[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

7

Reactant 5

HCID 11776TriphenylphosphineHCID 14798Sodium HydroxideHCID 789669-Borabicyclo(3.3.1)nonaneHCID 881004-Bromopyridinium chlorideHCID 17759473(S)-1,4-dibenzyl-2-vinylpiperazine

Product 1

HCID 69486583(S)-1,4-Dibenzyl-2-(2-pridin-4-yl-ethyl)-piperazineYield 56.4%

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

Prepared by the method in Example 128, using 9-borabicyclo[3.3.1]nonane (71.4 mL, 35.7 mmol, 0.5 M in THF), (S)-1,4-dibenzyl-2-vinyl-piperazine (2.61 g, 8.92 mmol), triphenylphosphine (749 mg, 2.86 mmol), tetrakis(triphenylphosphine)palladium(0) (413 mg, 0.36 mmol), 4-bromopyridine hydrochloride (2.60 g, 13.4 mmol) and 3M NaOH (10.4 mL, 31.2 mmol) to give the title compound (1.87 g, 56%): mp 96–98° C.; mass spectrum (ion spray): m/z=372 (M+1). Analysis calculated for C25H29N3: C, 80.82; H, 7.87; N, 11.31. Found: C, 80.80; H, 7.99; N, 11.18.

Workup

  1. customPrepared by the method in Example 128

Sources & evidence

ORD record
ord-05286bc5b1884bf381bbf434923bc566
Source dataset
uspto-grants-2007_05
Patent number
US07214673B2

Reaction notes

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