Benzyl 4-(3-nitropyridin-2-yl)piperazine-1-carboxylate → HCID 21477686, compound

HRID 864422Notes

Reaction equation

HRID 864422 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][N:14]([C:17]2[C:22]([N+:23]([O-])=O)=[CH:21][CH:20]=[CH:19][N:18]=2)[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>O1CCOCC1.[OH-].[Na+].[Cl-].[Cl-].[Cl-].[Ti+3]>[CH2:1]([O:8][C:9]([N:11]1[CH2:12][CH2:13][N:14]([C:17]2[C:22]([NH2:23])=[CH:21][CH:20]=[CH:19][N:18]=2)[CH2:15][CH2:16]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 1

HCID 21477687Benzyl 4-(3-nitropyridin-2-yl)piperazine-1-carboxylate

Product 1

HCID 21477686HCID 21477686, compound

Reagents, catalysts & solvents 3

HCID 10313229titanium(III) trichlorideCatalystHCID 14798Sodium HydroxideSolventHCID 312751,4-DioxaneSolvent

Procedure

1-[Benzyloxycarbonyl]-4-[3-nitro-2-pyridinyl]piperazine (PREPARATION 99), is dissolved in dioxane (923 ml) and cooled to 0°. Then aqueous titanium trichloride (20%, 555.3 ml) is added cautiously. After stirring 30 min the reaction is diluted with aqueous sodium hydroxide solution (2N, 1.5 l) and filtered through celite. The filter cake is washed with methanol/chloroform (10/90). The combined organic layers are washed with water, saline, dried and concentrated in vacuo to afford the desired product, NMR (300 MHz, CDCl3) 7.80, 7.38-7.32, 6.99, 6.88, 5.17, 3.67 and 3.12 δ.

Workup

  1. temperaturecooled to 0°
  2. filtrationfiltered through celite
  3. washThe filter cake is washed with methanol/chloroform (10/90)
  4. washThe combined organic layers are washed with water, saline
  5. customdried
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f1b645e842fe45fea43a5c4b9a799c07
Source dataset
uspto-grants-1996_10
Patent number
US05563142

Reaction notes

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