150515-80-3 → HCID 19023663, compound

HRID 2255437Notes

Reaction equation

HRID 2255437 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.Cl.[O:15]1[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2[CH:17]=[C:16]1[C:24]([NH:26][CH:27]1[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]1)=[O:25]>>[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[CH:4]([CH2:11][CH2:12][N:30]2[CH2:29][CH2:28][CH:27]([NH:26][C:24]([C:16]3[O:15][C:19]4[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=4[CH:17]=3)=[O:25])[CH2:32][CH2:31]2)[CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 19023659150515-80-3HCID 19023661HCID 19023661, compound

Product 1

HCID 19023663HCID 19023663, compoundYield 25.7%

Procedure

To a stirred solution of 2-(3,4-dihydro-2H-1-benzopyran-4-yl)ethanal (875 mg, 5 mmol) and 4-(2-benzofurancarboxamido) piperidine hydrochloride (1.4 g, 5 mmol) under a nitrogen atmosphere, borane/pyridine complex (0.5 ml, excess) was added. The reaction 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. The diethyl ether extracts were discarded. The acidic aqueous layer was basified by dropwise addition of 50% sodium hydroxide. The ethyl acetate layer was washed with distilled water, dried (Na2SO4), filtered and evaporated to afford an oily gum (520 mg). The resulting gum was purified by chromatography on silica (eluant: chloroform/ethanol/ammonium hydroxide; 85/14/1) to afford an oil (260 mg) which was crystallized from diethyl ether to afford the title compound (150 mg, 7%), mp=146-8°. Anal: C25H28N2O3 0.5 H2O, Calc. C, 72.62; H, 7.07; N, 6.77; Found C,72.40; H, 6.94; N, 6.83.

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 50% sodium hydroxide
  5. washThe ethyl acetate layer was washed with distilled water
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-ea3712dd4dd94858a5563bcc5ff1c4cb
Source dataset
uspto-grants-1993_08
Patent number
US05240943

Reaction notes

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