Sodium hydride → HCID 58409933, compound

HRID 1844900Notes

Reaction equation

HRID 1844900 reaction equation
O=[C:2]1[C:11]([C:12]#[N:13])=[C:10]([N:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)[C:9]2[CH2:8][CH2:7][C:6]3[CH:20]=[CH:21][CH:22]=[CH:23][C:5]=3[C:4]=2O1.[H-].[Na+]>C1COCC1>[N:14]1([C:10]2[C:9]3[CH2:8][CH2:7][C:6]4[C:20](=[CH:21][CH:22]=[CH:23][CH:5]=4)[C:4]=3[C:23]3[C:5]4[C:6]([CH2:20][C:2]=3[C:11]=2[C:12]#[N:13])=[CH:7][CH:8]=[CH:9][CH:4]=4)[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 16071709HCID 16071709, compound

Product 1

HCID 58409933HCID 58409933, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-oxo-4-(piperidin-1-yl)-5,6-dihydro-2H-benzo[h]chromene-3-carbonitrile (306 mg), indanone-2 (132 mg) and NaH (29 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 170-172° C.; IR (KBr) 2218 cm−1 (CN); MS (ESI) 377 (M++1); 1H NMR (200 MHz, CDCl3) δ 1.61-1.65 (m, 6H, 3CH2), 2.77-2.81 (m, 4H, 2CH2), 3.22-3.25 (m, 4H, 2CH2), 4.06 (s, 2H, 2CH2), 7.13-7.37 (m, 5H, ArH), 7.56 (d, J=7.21 Hz, 1H, ArH), 7.86-7.94 (m, 2H, ArH).

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-fc404c0c4dcf4219921f5d9970d6e2f6
Source dataset
uspto-grants-2015_02
Patent number
US08946682B2

Reaction notes

Loading…