Triethylamine → HCID 21504633, compound

HRID 1288225Notes

Reaction equation

HRID 1288225 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][CH:5]1[CH2:10][CH2:9][N:8]([S:11]([NH2:14])(=[O:13])=[O:12])[CH2:7][CH2:6]1.C(N(CC)CC)C.[Cl:22][C:23]1[CH:28]=[CH:27][N:26]=[C:25]([C:29](Cl)=[O:30])[CH:24]=1>Cl.O1CCCC1>[Cl:22][C:23]1[CH:28]=[CH:27][N:26]=[C:25]([C:29]([NH:2][CH2:3][CH2:4][CH:5]2[CH2:10][CH2:9][N:8]([S:11]([NH2:14])(=[O:13])=[O:12])[CH2:7][CH2:6]2)=[O:30])[CH:24]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 110951464-chloropyridine-2-carbonyl ChlorideHCID 1228207953750-64-4

Product 1

HCID 21504633HCID 21504633, compoundYield 36%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of 1.95 g. (0.008 mole) of 4-(2-aminoethyl)-1-piperidinesulfonamide hydrochloride and 2.22 ml. (0.016 mole) of triethylamine in 15 ml. of dry tetrahydrofuran, there were added 1.41 g. (0.008 mole) of 4-chloropicolinoyl chloride dissolved in 15 ml. of tetrahydrofuran. The initial addition step was slightly exothermic (~40° C.) and after completion of same, the resulting reaction mixture was stirred at ambient temperatures for a period of approximately 16 hours. At this point, the thoroughly stirred mixture was poured into 50 ml. of ice water and subsequently acidified with a few drops of 3N aqueous hydrochloric acid. The resulting crystalline precipitate was then recovered by means of suction filtration and thereafter recrystallized twice from acetonitrile to afford 0.997 g. of pure product. In this way, there was ultimately obtained a 36% of 4-[2-(4-chloropicolinamido)ethyl]-1-piperidinesulfonamide, m.p. 186°-187° C.

Workup

  1. additionTo a mixture of 1.95 g
  2. additionThe initial addition step
  3. custom(~40° C.)
  4. customafter completion of same, the resulting reaction mixture
  5. additionAt this point, the thoroughly stirred mixture was poured into 50 ml
  6. filtrationThe resulting crystalline precipitate was then recovered by means of suction filtration
  7. customrecrystallized twice from acetonitrile
  8. customto afford 0.997 g

Sources & evidence

ORD record
ord-4627c0877bd944ceadec2e5e00886e46
Source dataset
uspto-grants-1976_10
Patent number
US03987172

Reaction notes

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