Sodium hydride → HCID 58409942, compound

HRID 1844877Notes

Reaction equation

HRID 1844877 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:12]2[CH2:11][C:2]3[C:1](=[CH:10][CH:5]=[CH:4][CH:3]=3)[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 58409942HCID 58409942, 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-1 (132 mg) and NaH (39 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 136-138° C.; ESIMS 401 (M++1); IR (KBr) 2214 cm−1 (CN); HRMS calcd. for C2H24N2 400.1940 Found 400.1939.

Workup

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

Sources & evidence

ORD record
ord-09ab6418a39d4d54b008c011ecc69b57
Source dataset
uspto-grants-2015_02
Patent number
US08946682B2

Reaction notes

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