Sodium hydride → HCID 131720745, compound

HRID 965200Notes

Reaction equation

HRID 965200 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[H-].[Na+].C(C(Cl)C[O:31]CC(Cl)[CH:34]([C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)(C1C=CC=CC=1)C1C=CC=CC=1.N[C@H:50]([C:62]([OH:64])=[O:63])CC1C=C2C(C=CC=C2)=CC=1>CN(C=O)C>[C:41]1([CH:34]([C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)[O:63][CH2:62][CH2:50][O:1][C:2]2[CH:3]=[CH:4][C:5]([N:8]3[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]3)=[CH:6][CH:7]=2)[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=1.[C:62](=[O:63])([O-:31])[O-:64]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 92467p-(1-Piperazinyl)phenolHCID 1859152-NaphthylalanineHCID 67663942HCID 67663942, compound

Product 1

HCID 131720745HCID 131720745, compoundYield 202.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

4-(4-Hydroxyphenyl)piperazine (0.356 g, 2 mmol) is added to a stirred suspension of NaH (0.088 g of 60% oil dispersion (2.2 mmol)), washed and decanted with pentane) in DMF (5 mL) under N2 and the reaction mixture was heated to 70° C. for approximately 10 min (until the effervescence ceased). Benzhydrylchloroethylether (0.542 g, 2.2 mmol) in DMF (1.5 mL) was added, followed by Nal (0.331 g, 2.2 mmol). The reaction mixture was stirred and heated to 90°-100° C. for 48 h. DMF was removed in vacuo and the residue triturated in CHCl3. The insoluble solids removed by filtration, washed (CHCl3) and the combined organic extracts were washed with water, dried (Na2 SO4) and evaporated in vacuo to afford an oily residue (1 g). The residue is purified by column chromatography on silica gel using an increasing proportion of MeOH in CH2Cl2 containing 0.5% Et3N to give a colorless foamy solid (0.416 g, 53%). Traces of residual Et3N are removed by washing with CH2Cl2, dried (Na2SO4) and evaporation in vacuo to afford shiny crystalline flakes: mp 106°-108° C.: 1H NMR (DMSO-d6) d 9.14 (s, 1H), 7.4-7.2 (m, 10H), 6.91 (q, 4H), 5.57 (s, 1H), 4.12 (t, 2H), 3.71 (t, 2H), 3.21 (br s, 8H): IR 3361, 2925, 2834, 1674, 1516, 1496, 1452, 1252 cm-1. MS 389 (MH+). Anal. CaIc'd. for C25H28 N2O2 ·2 H2O: C, 64.18, H, 7.04, N, 5.76. Found: C, 64.49, H, 6.85, N, 6.06.

Workup

  1. washwashed
  2. customdecanted with pentane) in DMF (5 mL) under N2
  3. temperatureheated to 90°-100° C. for 48 h
  4. customDMF was removed in vacuo
  5. customthe residue triturated in CHCl3
  6. customThe insoluble solids removed by filtration
  7. washwashed (CHCl3)
  8. washthe combined organic extracts were washed with water
  9. customdried (Na2 SO4)
  10. customevaporated in vacuo

Sources & evidence

ORD record
ord-9f1e7e064090422cb79c9a39ba95177a
Source dataset
uspto-grants-1998_06
Patent number
US05773469

Reaction notes

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