Sodium hydride → HCID 58409940, compound

HRID 1844883Notes

Reaction equation

HRID 1844883 reaction equation
[C:1]1([C:11]2O[C:15](=O)[C:14]([C:18]#[N:19])=[C:13]([N:20]3[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]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+]>C1COCC1>[C:1]1([C:11]2[C:9]3[C:10]4[C:1](=[CH:2][CH:3]=[CH:4][CH:5]=4)[CH2:11][C:15]=3[C:14]([C:18]#[N:19])=[C:13]([N:20]3[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]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 2

HCID 24758Sodium hydrideHCID 120335292H-Pyran-3-carbonitrile, 6-(1-naphthalenyl)-2-oxo-4-(1-piperidinyl)-

Product 1

HCID 58409940HCID 58409940, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 6-(naphthalen-1-yl)-2-oxo-4-(piperidin-1-yl)-2H-pyran-3-carbonitrile (330 mg), indanone-2 (132 mg) and NaH (41 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 148-149° C.; ESIMS 401 (M+1); IR (KBr) 2213 cm−1 (CN); 13C NMR (75.53 MHz, CDCl3): δ 22.84, 24.94, 36.08, 52.16, 100.72, 116.12, 118.56, 120.75, 123.36, 124.30, 124.48, 124.92, 125.0, 125.36, 125.43, 127.09, 127.29, 130.15, 132.29, 132.64, 136.40, 138.86, 138.99, 140.82, 148.79, 153.65.

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-fecc40ce114b474c80c18610bfa1617b
Source dataset
uspto-grants-2015_02
Patent number
US08946682B2

Reaction notes

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