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

HRID 28225Notes

Reaction equation

HRID 28225 reaction equation
Cl.[C:2]([N:12]1[CH2:17][CH2:16][NH:15][CH:14]([C:18]([OH:20])=[O:19])[CH2:13]1)([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:3].Cl[C:22]1[C:27]([N+:28]([O-:30])=[O:29])=[CH:26][CH:25]=[CH:24][N:23]=1.C(N(CC)CC)C.Cl>O.CS(C)=O>[N+:28]([C:27]1[C:22]([N:15]2[CH2:16][CH2:17][N:12]([C:2]([O:4][CH2:5][C:6]3[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=3)=[O:3])[CH2:13][CH:14]2[C:18]([OH:20])=[O:19])=[N:23][CH:24]=[CH:25][CH:26]=1)([O-:30])=[O:29]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 796132-Chloro-3-nitropyridineHCID 450726774-((Benzyloxy)carbonyl)piperazine-2-carboxylic acid hydrochloride

Product 1

HCID 233397691-(3-Nitro-2-pyridinyl)-4-carbobenzoxypiperazine-2-carboxylic acid

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

A solution of 6.0 g. of 4-carbobenzoxypiperazine-2-carboxylic acid hydrochloride, 3.3 g. of 2-chloro-3-nitropyridine and 15 ml. of triethyl amine in 100 ml. of dimethyl sulfoxide is heated at 60° with stirring for 18 hours. The mixture is diluted with 400 ml. of water, acidified to pH 3 with concentrated hydrochloric acid, and extracted repeatedly with ether. The combined ether extracts are dried (MgSO4) and concentrated. The residue is crystallized from ethyl acetate/heptane to give 6.3 g. of the title product, m.p. 145°-147°.

Workup

  1. additionThe mixture is diluted with 400 ml
  2. extractionextracted repeatedly with ether
  3. dry with materialThe combined ether extracts are dried (MgSO4)
  4. concentrationconcentrated
  5. customThe residue is crystallized from ethyl acetate/heptane
  6. customto give 6.3 g

Sources & evidence

ORD record
ord-396650b65b9f408882dd6422b6698c7a
Source dataset
uspto-grants-1980_09
Patent number
US04225713

Reaction notes

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