Triphenylphosphine → 7-(4-Trifluoromethylbenzyloxy)-1-(4-methyl-1-piperazinyl)-naphthalene

HRID 235138Notes

Reaction equation

HRID 235138 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[C:9]2[N:12]2[CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][CH2:13]2)=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[F:38][C:39]([F:49])([F:48])[C:40]1[CH:47]=[CH:46][C:43]([CH2:44]O)=[CH:42][CH:41]=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[F:38][C:39]([F:48])([F:49])[C:40]1[CH:47]=[CH:46][C:43]([CH2:44][O:1][C:2]2[CH:11]=[C:10]3[C:5]([CH:6]=[CH:7][CH:8]=[C:9]3[N:12]3[CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][CH2:13]3)=[CH:4][CH:3]=2)=[CH:42][CH:41]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 676844-(Trifluoromethyl)benzenemethanolHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 108002178-(4-Methylpiperazin-1-yl)naphthalen-2-ol

Product 1

HCID 233535117-(4-Trifluoromethylbenzyloxy)-1-(4-methyl-1-piperazinyl)-naphthaleneYield 72.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of 7-hydroxy-1-(4-methyl-1-piperazinyl)-naphthalene (0.20 g, 0.83 mmol), triphenylphosphine (0.32 g, 1.22 mmol), and 4-trifluoromethylbenzyl alcohol (0.17 mL, 1.26 mmol)in dry THF (4 mL) was added diethyl azodicarboxylate in THF (1 mL). The mixture was stirred overnight at ambient temperature; then it was concentrated at reduced pressure. The residue was partitioned between ethyl acetate and 1N sodium hydroxide. The organic layer was washed with water and brine; then it was dried over magnesium sulfate and concentrated onto silica gel for flash chromatographic purification (1×6 inches). Elution with 75% ethyl acetate/hexane gave 0.24 g (72%) of the title compound as a nearly colorless oil. The oil was treated with HCl in ether to form the hydrochloride salt (0.23 g) which was recrystallized from chloroform/ether to give 0.14 g of a white solid thereof: mp 205°-206° C. Analysis calculated for C23H23F3N2O·HCl·0.25 H2O: C, 62.58; H, 5.59; N, 6.35. Found: C, 62.59; H, 5.63; N, 6.40.

Workup

  1. concentrationthen it was concentrated at reduced pressure
  2. customThe residue was partitioned between ethyl acetate and 1N sodium hydroxide
  3. washThe organic layer was washed with water and brine
  4. dry with materialthen it was dried over magnesium sulfate
  5. concentrationconcentrated onto silica gel for flash chromatographic purification (1×6 inches)
  6. washElution with 75% ethyl acetate/hexane

Sources & evidence

ORD record
ord-e2979c4f106144dc83276cd2d3f27c1e
Source dataset
uspto-grants-1997_01
Patent number
US05597826

Reaction notes

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