Tetrahydrofuran → HCID 58409918, compound

HRID 1844918Notes

Reaction equation

HRID 1844918 reaction equation
[N:1]1([C:7]2[CH:8]=[C:9]([C:22]3[S:23][CH:24]=[CH:25][CH:26]=3)[C:10]3[CH2:11][C:12]4[C:17]([C:18]=3[C:19]=2[C:20]#[N:21])=[CH:16][CH:15]=[CH:14][CH:13]=4)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].C1C[O:32]CC1>>[O:32]=[C:11]1[C:10]2[C:9]([C:22]3[S:23][CH:24]=[CH:25][CH:26]=3)=[CH:8][C:7]([N:1]3[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]3)=[C:19]([C:20]#[N:21])[C:18]=2[C:17]2[C:12]1=[CH:13][CH:14]=[CH:15][CH:16]=2

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 58409928HCID 58409928, compound

Product 1

HCID 58409918HCID 58409918, compoundYield 89%

Conditions

Temperature
2.5 °C

Procedure

A solution of 3-(piperidin-1-yl)-1-(thiophen-2-yl)-9H-fluorene-4-carbonitrile (356 mg) in THF was added sodium hydride (38 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. Yellow solid; yield 89%; mp 172-174° C.; ESMS 371 (M++1); IR (KBr) 1703 cm−1 (CO), 2218 (CN); 1H NMR (300 MHz, CDCl3) δ 1.66-1.75 (m, 2H, CH2), 1.81-1.90 (m, 4H, 2CH2), 3.38-3.44 (m, 4H, 2CH2), 6.88 (s, 1H, ArH), 7.18 (dd, J=8.85 Hz & J=3.75 Hz, 1H, ArH), 7.44 (t, J=7.5 Hz, 1H, ArH), 7.48 (d, J=6 Hz, 1H, CH), 7.59 (t, J=7.6 Hz, 1H, ArH), 7.68 (d, J=7.2 Hz, 1H, ArH), 7.84 (d, J=4.7 Hz, 1H, CH), 8.38 (d, J=7.5 Hz, 1H, CH).

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-d62b034eaba9446a946c2630d2e16bfc
Source dataset
uspto-grants-2015_02
Patent number
US08946682B2

Reaction notes

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