Triethylamine → 1-(2-Nitro-3-pyridinyl)-4-carbobenzoxypiperazine-2-carboxylic acid

HRID 28226

Reaction equation

HRID 28226 reaction equation
[N+:1]([C:4]1[C:9](F)=[CH:8][CH:7]=[CH:6][N:5]=1)([O-:3])=[O:2].Cl.[C:12]([N:22]1[CH2:27][CH2:26][NH:25][CH:24]([C:28]([OH:30])=[O:29])[CH2:23]1)([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13].C(N(CC)CC)C>CS(C)=O>[N+:1]([C:4]1[C:9]([N:25]2[CH2:26][CH2:27][N:22]([C:12]([O:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[O:13])[CH2:23][CH:24]2[C:28]([OH:30])=[O:29])=[CH:8][CH:7]=[CH:6][N:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27628023-Fluoro-2-nitropyridineHCID 450726774-((Benzyloxy)carbonyl)piperazine-2-carboxylic acid hydrochloride

Product 1

HCID 233397631-(2-Nitro-3-pyridinyl)-4-carbobenzoxypiperazine-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 2.8 g. of 2-nitro-3-fluoropyridine, 5.0 g. of 4-carbobenzoxypiperazine-2-carboxylic acid, hydrochloride, 25 ml. of triethylamine, and 90 ml. of dimethyl sulfoxide is heated at 55° with stirring for 11/2 hours, then allowed to stand at room temperature overnight. A similar workup to that described in Example 1 gives 4.5 g. of the title product as a viscous orange glass. Thin layer chromatographic analysis of this material shows one single spot.

Workup

  1. additionA mixture of 2.8 g
  2. waitto stand at room temperature overnight
  3. customgives 4.5 g

Sources & evidence

ORD record
ord-b065c219fde744c78b1c93192600a75d
Source dataset
uspto-grants-1980_09
Patent number
US04225713

Linked notes

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