Tetrahydrofuran → HCID 58409906, compound

HRID 1844911Notes

Reaction equation

HRID 1844911 reaction equation
[N:1]1([C:7]2[CH:19]=[C:18]([C:20]3[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=3)[C:17]3[C:16]4[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=4)[CH2:10][C:9]=3[C:8]=2[C:27]#[N:28])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].C1C[O:34]CC1>>[O:34]=[C:10]1[C:9]2[C:8]([C:27]#[N:28])=[C:7]([N:1]3[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]3)[CH:19]=[C:18]([C:20]3[CH:21]=[CH:22][C:23]([CH3:26])=[CH:24][CH:25]=3)[C:17]=2[C:16]2[C:11]1=[CH:12][CH:13]=[CH:14][CH:15]=2

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 58409939HCID 58409939, compound

Product 1

HCID 58409906HCID 58409906, compound

Conditions

Temperature
2.5 °C

Procedure

A solution of 2-(piperidin-1-yl)-4-p-tolyl-9H-fluorene-1-carbonitrile (364 mg) in THF was added sodium hydride (40 mg) and was stirred at 0-5° C. for less than five minutes. After completion, the reaction solvent was evaporated under vacuum and the crude solid obtained was quenched with ice water and subsequently neutralized by dilute HCl. The precipitate thus obtained was filtered and purified on a silica gel column using ethyl acetate-hexane as eluent. Red solid; mp 230-232° C.; ESMS 379 (M++1); IR (KBr) 1703 cm−1 (CO), 2219 (CN); 1H NMR (300 MHz, CDCl3) δ 1.60-1.64 (m, 2H, CH2), 1.79-1.84 (m, 4H, 2CH2), 2.48 (s, 3H, CH3), 3.19-3.24 (m, 4H, 2CH2), 6.65-6.70 (m, 1H, ArH), 6.87 (s, 1H, ArH), 7.14-7.19 (m, 2H, ArH), 7.28-7.33 (m, 4H, ArH), 7.63-7.67 (m, 1H, ArH). HRMS calcd. for C26H22N2O 378.1732 found 378.1728.

Workup

  1. customAfter completion, the reaction solvent was evaporated under vacuum
  2. customthe crude solid obtained
  3. customwas quenched with ice water
  4. customThe precipitate thus obtained
  5. filtrationwas filtered
  6. custompurified on a silica gel column

Sources & evidence

ORD record
ord-aec5117bed7549ed8307fc18a64b9786
Source dataset
uspto-grants-2015_02
Patent number
US08946682B2

Reaction notes

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