Nicotinic Acid → HCID 53666820, compound

HRID 362958Notes

Reaction equation

HRID 362958 reaction equation
C1(N=C=NC2CCCCC2)CCCCC1.[NH2:16][CH2:17][CH2:18][O:19][CH2:20][CH:21]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[OH:22].[C:29](O)(=[O:36])[C:30]1[CH:35]=[CH:34][CH:33]=[N:32][CH:31]=1.ON1C2C=CC=CC=2N=N1>O1CCCC1.C(OCC)(=O)C.C(N(CC)CC)C>[C:29]([NH:16][CH2:17][CH2:18][O:19][CH2:20][CH:21]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[OH:22])(=[O:36])[C:30]1[CH:35]=[CH:34][CH:33]=[N:32][CH:31]=1

Participants

8

Reactant 4

HCID 938Nicotinic AcidHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 10464936HCID 10464936, compound

Product 1

HCID 53666820HCID 53666820, compoundYield 23.6%

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

1.23 g of N,N'-dicyclohexylcarbodiimide was added, with ice cooling, to a solution of 1.08 g of 2-(2-aminoethoxy)-1-phenylethanol, 730 mg of nicotinic acid, 810 mg of 1-hydroxybenzotriazole and 0.83 ml of triethylamine dissolved in 5 ml of tetrahydrofuran. The resulting mixture was stirred at the same temperature for 5 minutes and further at room temperature for 1 hour. To the reaction mixture was added 11 ml of ethyl acetate. The insolubles were removed by filtration. To the filtrate was added 5 ml of water and the mixture was adjusted to pH 2 with 6N hydrochloric acid. The aqueous layer was separated. The organic layer was extracted with 5 ml of water. The extract was combined with the previously separated aqueous layer. The combined aqueous layer was mixed with 20 ml of chloroform and adjusted to pH 10 with potassium carbonate. The organic layer was separated, washed with water, and dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. The residue thus obtained was purified by column chromatography (eluant: chloroform/ethanol=15/1) to obtain 400 mg of oily 2-(2-nicotinoylamino-ethoxy)-1-phenylethanol (compound No. 216).

Workup

  1. customThe insolubles were removed by filtration
  2. additionTo the filtrate was added 5 ml of water
  3. customThe aqueous layer was separated
  4. extractionThe organic layer was extracted with 5 ml of water
  5. additionThe combined aqueous layer was mixed with 20 ml of chloroform
  6. customThe organic layer was separated
  7. washwashed with water
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customThe solvent was removed by distillation under reduced pressure
  10. customThe residue thus obtained
  11. customwas purified by column chromatography (eluant: chloroform/ethanol=15/1)

Sources & evidence

ORD record
ord-812b5730d62146e8a6ca8b4cc825cf89
Source dataset
uspto-grants-1999_02
Patent number
US05872117

Reaction notes

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