HCID 19023661, compound → HCID 19023662, compound

HRID 2255436Notes

Reaction equation

HRID 2255436 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[CH:4]([CH2:11][CH:12]=O)[CH2:3][CH2:2]1.[C:14]([NH:17][CH:18]1[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1)(=[O:16])[CH3:15].CC(O)=O>C(O)C>[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[CH:4]([CH2:11][CH2:12][N:21]2[CH2:22][CH2:23][CH:18]([NH:17][C:14](=[O:16])[CH3:15])[CH2:19][CH2:20]2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 19023661HCID 19023661, compoundHCID 70155070HCID 70155070, compound

Product 1

HCID 19023662HCID 19023662, compoundYield 82.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of 2-(3,4-dihydro-2H-1-benzopyran-4-yl]ethanal (2.50 g, 14.28 mmol) and 4-acetamidopiperidine AcOH (2.88 g, 14.28 mmol) (preparation described in U.S. Pat. No. 5,028,616) in ethanol (80 ml) under a nitrogen atmosphere, borane/pyridine complex (1.5 ml, 15 mmol) was added. The reaction mixture was stirred overnight (ca 15 h) and evaporated to an oily gum which was neutralized by careful addition of 10% hydrochloric acid. The acidic solution was extracted with diethyl ether and the diethyl ether extracts were discarded. The acidic aqueous layer was basified by dropwise addition of a 50% sodium hydroxide solution. The basic solution (>pH 12) was extracted with ethyl acetate. The ethyl acetate layer was washed with distilled water, dried (Na2SO4), filtered and evaporated to afford an oily gum (3.56 g). The resulting gum was purified by chromatography on silica (eluant: chloroform/ethanol/ammonium hydroxide; 85/14/1) to afford an oil (2.56 g) which was crystallized from diethyl ether to afford the title compound (2.40 g, 56%) mp=126-8°. Anal: C18H26N2O2Calc.: C 71.49; H 8.67; N 9.26; Found C 71.46; H 8.84; N 9.26.

Workup

  1. customevaporated to an oily gum which
  2. additionwas neutralized by careful addition of 10% hydrochloric acid
  3. extractionThe acidic solution was extracted with diethyl ether
  4. additionThe acidic aqueous layer was basified by dropwise addition of a 50% sodium hydroxide solution
  5. extractionThe basic solution (>pH 12) was extracted with ethyl acetate
  6. washThe ethyl acetate layer was washed with distilled water
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-674ccddb174b4a7c8c5eb7e56a3b9031
Source dataset
uspto-grants-1993_08
Patent number
US05240943

Reaction notes

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