Lithium Chloride → HCID 21093754, compound

HRID 1349943Notes

Reaction equation

HRID 1349943 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([N+:24]([O-:26])=[O:25])[C:5]([O:22]C)=[C:6]([CH:21]=1)[CH:7]=[C:8]1[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]1.[Cl-].[Li+]>CN(C)C=O>[Br:1][C:2]1[CH:3]=[C:4]([N+:24]([O-:26])=[O:25])[C:5]([OH:22])=[C:6]([CH:21]=1)[CH:7]=[C:8]1[CH2:9][CH2:10][N:11]([C:14]([O:16][C:17]([CH3:18])([CH3:19])[CH3:20])=[O:15])[CH2:12][CH2:13]1

Participants

4

Reactant 2

HCID 433294Lithium ChlorideHCID 21093755HCID 21093755, compound

Product 1

HCID 21093754HCID 21093754, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of tert-butyl 4-(5-bromo-2-methoxy-3-nitrobenzylidene)piperidine-1-carboxylate (2.5 g, 5.9 mmol) and lithium chloride (1 g) in anhydrous N,N-dimethylformamide was stirred at 120° C. for 4 h. It was allowed to cool to room temperature and evaporated in vacuo. The residue was treated with water (50 mL) and extracted with diethyl ether (2×100 mL). The combined organic layers was washed with water (50 mL) and dried (Na2SO4). Evaporation of solvent gave the title compound as a crude oil (2.1 g).

Workup

  1. temperatureto cool to room temperature
  2. customevaporated in vacuo
  3. additionThe residue was treated with water (50 mL)
  4. extractionextracted with diethyl ether (2×100 mL)
  5. washThe combined organic layers was washed with water (50 mL)
  6. dry with materialdried (Na2SO4)
  7. customEvaporation of solvent

Sources & evidence

ORD record
ord-9fc2eb7150994e1ea81f17e381821bce
Source dataset
uspto-grants-2007_05
Patent number
US07214674B2

Reaction notes

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