Tetrahydrofuran → HCID 58409951, compound

HRID 1844905Notes

Reaction equation

HRID 1844905 reaction equation
[C:1]1([C:11]2[C:23]3[C:22]4[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=4)[CH2:16][C:15]=3[C:14]([C:24]#[N:25])=[C:13]([N:26]3[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]3)[CH:12]=2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[H-].[Na+].C1C[O:37]CC1>>[C:1]1([C:11]2[C:23]3[C:22]4[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=4)[C:16](=[O:37])[C:15]=3[C:14]([C:24]#[N:25])=[C:13]([N:26]3[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]3)[CH:12]=2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 58409940HCID 58409940, compound

Product 1

HCID 58409951HCID 58409951, compound

Conditions

Temperature
2.5 °C

Procedure

A solution of 4-(naphthalen-1-yl)-2-(piperidin-1-yl)-9H-fluorene-1-carbonitrile (400 mg) in THF was added sodium hydride (37 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 202-204° C.; ESIMS 0.415 (M++1); IR (KBr) 2221 (CN), 1719 cm−1 (CO), HRMS calcd. for C29H22N2O 414.1732. Found 414.1714.

Workup

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

Sources & evidence

ORD record
ord-d508d1c0f24f444fbbf058540c319d47
Source dataset
uspto-grants-2015_02
Patent number
US08946682B2

Reaction notes

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