Sodium hydride → HCID 58409926, compound

HRID 1844902Notes

Reaction equation

HRID 1844902 reaction equation
[CH3:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]2[C:17]3[CH2:16][CH2:15][C:14]4[CH:18]=[CH:19][CH:20]=[CH:21][C:13]=4[C:12]=3O[C:10](=O)[C:9]=2[C:23]#[N:24])[CH2:4][CH2:3]1.[H-].[Na+]>C1COCC1>[CH3:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]2[C:17]3[CH2:16][CH2:15][C:14]4[C:13](=[CH:21][CH:20]=[CH:19][CH:18]=4)[C:12]=3[C:21]3[C:13]4[C:14]([CH2:18][C:10]=3[C:9]=2[C:23]#[N:24])=[CH:15][CH:16]=[CH:17][CH:12]=4)[CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 16216253HCID 16216253, compound

Product 1

HCID 58409926HCID 58409926, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4-(4-methylpiperidin-1-yl)-2-oxo-5,6-dihydro-2H-benzo[h]chromene-3-carbonitrile (320 mg), indanone-2 (132 mg) and NaH (36 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 152-154° C.; IR (KBr) 2212 cm−1 (CN); MS (ESI) 391 (M+11).

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-af45634a030d49829eb9122e1ee6e808
Source dataset
uspto-grants-2015_02
Patent number
US08946682B2

Reaction notes

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