Sodium hydride → HCID 58409952, compound

HRID 1844876Notes

Reaction equation

HRID 1844876 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:12]3[CH2:11][C:1]4[C:2](=[CH:3][CH:4]=[CH:5][CH:10]=4)[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 58409952HCID 58409952, 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-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 188-190° C.; ESIMS 401 (M++1); IR (KBr) 2214 cm−1 (CN); 13C NMR (75.53 MHz, CDCl3): δ 22.86, 25.03, 34.33, 52.76, 97.13, 116.68, 117.50, 121.36, 123.53, 124.14, 124.34, 124.87, 124.91, 125.22, 125.94, 127.00, 127.19, 127.25, 129.68, 132.40, 135.37, 136.53, 138.21, 141.05, 143.26, 143.37, 156.43.

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-5d615fd79ff3459d8e93935a27285b17
Source dataset
uspto-grants-2015_02
Patent number
US08946682B2

Reaction notes

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