Triphenylphosphine → HCID 10085886, compound

HRID 854320Notes

Reaction equation

HRID 854320 reaction equation
[N:1]([CH2:4][CH:5]1[CH2:10][N:9]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:8][CH2:7][N:6]1[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O>[CH2:18]([N:6]1[CH2:7][CH2:8][N:9]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:10][CH:5]1[CH2:4][NH2:1])[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 10381414HCID 10381414, compound

Product 1

HCID 10085886HCID 10085886, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2azidomethyl-1,4-dibenzyl-piperazine (9.0 g, 0.028 mol) in TBFE (90 mL) and water (5 mL) was added triphenylphosphine (22.3 g, 0.085 mol) and the mixture stirred for 18 h. The reaction was concentrated to an oil, dissolved in 1N hydrochloric acid (100 mL) and washed with ethyl acetate (2×100 mL). The acidic aqueous layer was cooled to 0° C. and the pH adjusted to 8.5 with 3N sodium hydroxide. The mixture was extracted with ethyl acetate (2×100 mL) and extracts dried over sodium sulfate and concentrated to an oil.

Workup

  1. concentrationThe reaction was concentrated to an oil
  2. dissolutiondissolved in 1N hydrochloric acid (100 mL)
  3. washwashed with ethyl acetate (2×100 mL)
  4. extractionThe mixture was extracted with ethyl acetate (2×100 mL)
  5. dry with materialextracts dried over sodium sulfate
  6. concentrationconcentrated to an oil

Sources & evidence

ORD record
ord-fc3842f9e7694ebca75076a81b612232
Source dataset
uspto-grants-2007_08
Patent number
US07259157B2

Reaction notes

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