Tetrahydrofuran → HCID 58409913, compound

HRID 1844914Notes

Reaction equation

HRID 1844914 reaction equation
[C:1]1([C:7]2[C:19]3[CH2:18][C:17]4[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=4)[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:18]1[C:19]2[C:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)=[CH:8][C:9]([N:22]3[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]3)=[C:10]([C:20]#[N:21])[C:11]=2[C:12]2[C:17]1=[CH:16][CH:15]=[CH:14][CH:13]=2

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 58409927HCID 58409927, compound

Product 1

HCID 58409913HCID 58409913, compound

Conditions

Temperature
2.5 °C

Procedure

A solution of 1-phenyl-3-(piperidin-1-yl)-9H-fluorene-4-carbonitrile (350 mg) in THF was added sodium hydride (34 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 166-168° (C; ESIMS 365 (M++1); IR (KBr) 2219 (CN), 1705 cm−1 (CO); 13C NMR (75.53 MHz, CDCl3): δ 22.68, 24.67, 51.55, 95.24, 115.94, 118.11, 120.97, 121.16, 122.41, 126.70, 127.64, 129.33, 133.10, 133.94, 135.61, 139.20, 145.60, 149.61, 158.96, 188.36.

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-04b7c99077fb4884a0eea7860fb24d6a
Source dataset
uspto-grants-2015_02
Patent number
US08946682B2

Reaction notes

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