Tetrahydrofuran → HCID 58409947, compound

HRID 1844919Notes

Reaction equation

HRID 1844919 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:20]3[CH2:19][C:18]4[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=4)[C:12]=3[C:11]([C:21]#[N:22])=[C:10]([N:23]3[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]3)[CH:9]=2)=[CH:4][CH:3]=1.[H-].[Na+].C1C[O:34]CC1>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:20]3[C:19](=[O:34])[C:18]4[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=4)[C:12]=3[C:11]([C:21]#[N:22])=[C:10]([N:23]3[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]3)[CH:9]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 58409938HCID 58409938, compound

Product 1

HCID 58409947HCID 58409947, compoundYield 91%

Procedure

A solution of 1-(4-fluorophenyl)-3-(piperidin-1-yl)-9H-fluorene-4-carbonitrile (368 mg) in THF was added sodium hydride (38 mg) and was stirred at room temperature 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. Yellow solid; yield 91%; mp 180-182° C.; ESMS 383 (M++1); IR (KBr) 1707 cm−1 (CO), 2219 (CN); 1H NMR (300 MHz, CDCl3) δ 1.69-1.75 (m, 2H, CH2), 1.80-1.89 (m, 4H, 2CH2), 3.39-3.44 (m, 4H, 2CH2), 6.63 (s, 1H, ArH), 7.16 (t, J=8.6 Hz, 2H, ArH), 7.41 (t, J=7.6 Hz, 1H, ArH), 7.46-7.53 (m, 2H, ArH), 7.56-7.65 (m, 2H, ArH), 8.37 (d, J=7.6 Hz, 1H, ArH).

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-da49370ac92b4289a0959da0920548c2
Source dataset
uspto-grants-2015_02
Patent number
US08946682B2

Reaction notes

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