Piperidine → 5-(p-Cyanophenyl)-4-pentynoic acid

HRID 1588090

반응식

HRID 1588090 반응식
[C:1]([OH:7])(=[O:6])[CH2:2][CH2:3][C:4]#[CH:5].Br[C:9]1[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[CH:11][CH:10]=1.N1CCCCC1>C(OCC)(=O)C.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:13]([C:12]1[CH:15]=[CH:16][C:9]([C:5]#[C:4][CH2:3][CH2:2][C:1]([OH:7])=[O:6])=[CH:10][CH:11]=1)#[N:14]

참가 물질

6

반응물 3

HCID 8082PiperidineHCID 12162Benzonitrile, 4-bromo-HCID 224644-Pentynoic acid

생성물 1

HCID 189975535-(p-Cyanophenyl)-4-pentynoic acid

시약·촉매·용매 2

HCID 11979704Tetrakis(triphenylphosphine)palladium촉매HCID 8857Ethyl Acetate용매

반응 조건

온도
80 °C

실험 절차

A solution of 4-pentynoic acid (2.15 g, 22 mmol), 4-bromobenzonitrile (3.64 g, 20 mmol) and piperidine (40 mL) was degassed by bubbling nitrogen through the solution for 5 min prior to the addition of tetrakis(triphenylphosphine) palladium (0) (240 mg, 0.2 mmol). The reaction vial was sealed and warmed to 80° C. for 1.5 h. After cooling to 23° C., the reaction mixture was diluted with ethyl acetate (200 mL), filtered, and concentrated in vacuo. The residue was diluted with ethyl acetate (300 mL), washed with 5% HCl (2×100 mL), washed with water (1×100 mL), and extracted with 3% sodium carbonate (2×200 mL). The basic aqueous layer was treated with decolorizing carbon, filtered, and acidified to pH=2. The resultant solid was filtered, washed with water, dried, and purified by flash chromatography (gradient ethyl acetate:methylene chloride:acetic acid 1:9:0.005) and fractional recrystallization (methylene chloride-ether) to afford the title compound as a white solid: m.p. 149°-152° C.

후처리

  1. customby bubbling nitrogen through the solution for 5 min
  2. customThe reaction
  3. customvial was sealed
  4. temperatureAfter cooling to 23° C.
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. additionThe residue was diluted with ethyl acetate (300 mL)
  8. washwashed with 5% HCl (2×100 mL)
  9. washwashed with water (1×100 mL)
  10. extractionextracted with 3% sodium carbonate (2×200 mL)
  11. additionThe basic aqueous layer was treated with decolorizing carbon
  12. filtrationfiltered
  13. filtrationThe resultant solid was filtered
  14. washwashed with water
  15. customdried
  16. custompurified by flash chromatography (gradient ethyl acetate:methylene chloride:acetic acid 1:9:0.005) and fractional recrystallization (methylene chloride-ether)

출처 및 근거

ORD 기록
ord-6aa20b7bc1484ee0b1ce5b23f7ddf07f
출처 데이터셋
uspto-grants-1993_06
특허 번호
US05220050

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