Tetrahydrofuran → HCID 58409916, compound

HRID 1844904Notes

Reaction equation

HRID 1844904 reaction equation
[C:1]1([C:7]2[C:19]3[C:18]4[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=4)[CH2:12][C:11]=3[C:10]([C:20]#[N:21])=[C:9]([N:22]3[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]3)[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].C1C[O:33]CC1>>[O:33]=[C:12]1[C:11]2[C:10]([C:20]#[N:21])=[C:9]([N:22]3[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]3)[CH:8]=[C:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[C:19]=2[C:18]2[C:13]1=[CH:14][CH:15]=[CH:16][CH:17]=2

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 58409936HCID 58409936, compound

Product 1

HCID 58409916HCID 58409916, compound

Conditions

Temperature
2.5 °C

Procedure

A solution of 4-phenyl-2(piperidin-1-yl)-9H-fluorene-1-carbonitrile (350 mg) in THF was added sodium hydride (27 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. Light red solid; mp 220-222° C.; ESIMS 365 (M++1); IR (KBr) 2220 (CN), 1709 cm−1 CO).

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-fd30b982c9b74e99bd585f62276ad16f
Source dataset
uspto-grants-2015_02
Patent number
US08946682B2

Reaction notes

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