Tetrahydrofuran → HCID 58409943, compound

HRID 1844915Notes

Reaction equation

HRID 1844915 reaction equation
[C:1]1([C:11]2[C:23]3[CH2:22][C:21]4[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=4)[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](=[O:37])[C:21]4[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=4)[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 58409952HCID 58409952, compound

Product 1

HCID 58409943HCID 58409943, compound

Conditions

Temperature
2.5 °C

Procedure

A solution of 1-(naphthalen-1-yl)-3-(piperidin-1-yl)-9H-fluorene-4-carbonitrile (400 mg) in THF was added sodium hydride (39 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; mp 180-182° C.; ESIMS 415 (M-+1); IR (KBr) 2213 (CN), 1707 cm−1 (CO); 13C NMR (75.53 MHz, CDCl3): δ 22.65, 24.68, 51.57, 95.45, 115.96, 118.89, 121.27, 122.49, 122.80, 123.78, 123.92, 124.68, 124.78, 125.04, 127.22, 127.57, 129.35, 130.02, 132.05, 133.10, 133.93, 134.13, 139.41, 143.51, 149.06, 158.86, 187.99.

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-cc8a69a3838f418e867e4d83cf26b898
Source dataset
uspto-grants-2015_02
Patent number
US08946682B2

Reaction notes

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