Ethylene Glycol → HCID 14773856, compound

HRID 1199936Notes

Reaction equation

HRID 1199936 reaction equation
[C:1]([C:3]1[C:12](=[O:13])[N:11]2[C:6]([CH:7]=[CH:8][CH:9]=[CH:10]2)=[C:5]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:4]=1[N:19]1[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1)#[N:2].[H-].[Na+].C(O)C[OH:29]>>[C:1]([C:3]1[C:12](=[O:13])[N:11]2[C:6]([CH:7]=[CH:8][CH:9]=[CH:10]2)=[C:5]([C:14]([O:16][CH2:17][CH2:18][OH:29])=[O:15])[C:4]=1[N:19]1[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1)#[N:2]

Participants

4

Reactant 3

HCID 174Ethylene GlycolHCID 24758Sodium hydrideHCID 14551507HCID 14551507, compound

Product 1

HCID 14773856HCID 14773856, compound

Conditions

Temperature
100 °C

Procedure

To a solution of 1.10 g of 3-cyano-1-ethoxycarbonyl-2-piperidino-4H-quinolizin-4-one (Example 6, S-35) in 30 ml of ethylene glycol was added 150 mg of 60% sodium hydride, and the reaction mixture was stirred at 100° C. for 14 hours. After cooling, the precipitated crystals were collected by filtration and then the crude crystals were chromatographed on a silica gel column using a mixed solvent of dichloromethane and diethyl ether (1:1) as an eluent to obtain 180 mg of 3-cyano-1-(2-hydroxyethoxycarbonyl)-2-piperidino-4H-quinolizin-4-one.

Workup

  1. temperatureAfter cooling
  2. filtrationthe precipitated crystals were collected by filtration
  3. customthe crude crystals were chromatographed on a silica gel column

Sources & evidence

ORD record
ord-07032946219d4e70ad6a80cdd5fa3b22
Source dataset
uspto-grants-1990_02
Patent number
US04904657

Reaction notes

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