Sodium hydride → HCID 58409919, compound

HRID 1844884Notes

Reaction equation

HRID 1844884 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]1O[C:15](=O)[C:14]([C:18]#[N:19])=[C:13]([N:20]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)[CH:12]=1.[H-].[Na+]>C1COCC1>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]1[C:9]2[C:10]3[C:5](=[CH:4][CH:3]=[CH:2][CH:1]=3)[CH2:6][C:15]=2[C:14]([C:18]#[N:19])=[C:13]([N:20]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)[CH:12]=1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 110888242H-Pyran-3-carbonitrile, 6-(2-naphthalenyl)-2-oxo-4-(1-piperidinyl)-

Product 1

HCID 58409919HCID 58409919, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 6-(naphthalen-2-yl)-2-oxo-4-(piperidin-1-yl)-2H-pyran-3-carbonitrile (330 mg), indanone-2 (132 mg) and NaH (43 mg) in THF was stirred for <5 min. After completion, the reaction solvent was evaporated under vacuum to dryness and crude solid was quenched with ice water and subsequently neutralized with dil. HCl, finally purified by column chromatography using ethylacetate-hexane as eluent. White solid; mp 142-144° C.; ESIMS 401 (M++1); IR (KBr) 2215 cm−1 (CN).

Workup

  1. customAfter completion, the reaction solvent was evaporated under vacuum to dryness
  2. customcrude solid was quenched with ice water
  3. customfinally purified by column chromatography

Sources & evidence

ORD record
ord-83a15ec41b294bc1ab58eaf8956232b4
Source dataset
uspto-grants-2015_02
Patent number
US08946682B2

Reaction notes

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