Oxalyl chloride → HCID 15166371, compound

HRID 1195669Notes

Reaction equation

HRID 1195669 reaction equation
[N:1]1[O:5][N:4]=[C:3]2[CH:6]=[C:7]([C:10]([OH:12])=O)[CH:8]=[CH:9][C:2]=12.C(Cl)(=O)C(Cl)=O.[NH2:19][CH2:20][CH:21]1[CH2:26][CH2:25][N:24]([CH2:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][N:30]=2)[CH2:23][CH2:22]1>C(Cl)Cl.CN(C)C=O>[N:1]1[O:5][N:4]=[C:3]2[CH:6]=[C:7]([C:10]([NH:19][CH2:20][CH:21]3[CH2:26][CH2:25][N:24]([CH2:27][CH2:28][C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][N:30]=4)[CH2:23][CH2:22]3)=[O:12])[CH:8]=[CH:9][C:2]=12

Participants

6

Reactant 3

HCID 65578Oxalyl chlorideHCID 27354542,1,3-Benzoxadiazole-5-carboxylic acidHCID 15166360HCID 15166360, compound

Product 1

HCID 15166371HCID 15166371, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of benzofurazan-5-carboxylic acid (150 mg, 0.91 mmol) in methylene chloride (3.3 ml) was added dimethylformamide (1 drop) followed by dropwise addition of oxalyl chloride (89 μl, 1.0 mmol). The resulting solution was stirred at room temperature for 3 hours and then concentrated under reduced pressure. The brown oil was redissolved in methylene chloride (3.3 ml) and was added to a cooled (0° C.) solution of 4-(aminomethyl)-1-(2-pyridylethyl)piperidine (0.21 g, 0.95 mmol) in methylene chloride (1.6 ml). The reaction mixture was stirred at 0° C. for 11/2 hours. Solvent evaporation, flash chromatography (silica gel, chloroform-methanol-ammonium hydroxide, 95/5/1/2) and trituration with hexane-ethyl acetate gave 4-[N-(benzofurazan-5-carbonyl)aminomethyl]-1-(2-pyridylethyl)piperidine (133 mg, 40%);

Workup

  1. concentrationconcentrated under reduced pressure
  2. dissolutionThe brown oil was redissolved in methylene chloride (3.3 ml)
  3. additionwas added to
  4. stirringThe reaction mixture was stirred at 0° C. for 11/2 hours
  5. customSolvent evaporation, flash chromatography (silica gel, chloroform-methanol-ammonium hydroxide, 95/5/1/2) and trituration with hexane-ethyl acetate

Sources & evidence

ORD record
ord-7c34f8a7349e4d56b7d3c669edb415c7
Source dataset
uspto-grants-1992_05
Patent number
US05112824

Reaction notes

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