Hydrochloric Acid → 3-Aminomethyl-1-(p-chlorobenzyl)piperidine

HRID 133584

반응식

HRID 133584 반응식
[C:1]([CH:4]1[CH2:9][CH2:8][CH2:7][N:6]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=2)[CH2:5]1)(=O)[NH2:2].B.C1COCC1.Cl.[OH-].[Na+]>C1COCC1>[NH2:2][CH2:1][CH:4]1[CH2:9][CH2:8][CH2:7][N:6]([CH2:10][C:11]2[CH:12]=[CH:13][C:14]([Cl:17])=[CH:15][CH:16]=2)[CH2:5]1

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 2723981Borane;tetrahydrofuranHCID 28457973-Carbamoyl-1-(4-chlorobenzyl)piperidine

생성물 1

HCID 184262223-Aminomethyl-1-(p-chlorobenzyl)piperidine

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
70 °C

실험 절차

3-Carbamoyl-1-(4-chlorobenzyl)piperidine (3.80 g, 15 mmol) was dissolved in THF (30 mL), and 1 M BH3-THF (9.4 mL) was added to the obtained solution. The resulting mixture was stirred at 70° C. for 15 hours. After cooling to 0° C., a 2 M hydrochloric acid (50 mL) was added, and the mixture was stirred at room temperature for another 3 hours, basicified with an 4 M aqueous solution of NaOH and extracted with ethyl acetate (100 mL×3). The extracts were combined, washed with brine, dried over anhydrous Na2SO4, filtered and concentrated. The obtained crude product was purified by column chromatography (SiO2, ethyl acetate/ethanol/triethylamine=80:15:5) to thereby provide 3-(aminomethyl)-1-(4-chlorobenzyl)piperidine (2.05 g, 55%). 1H NMR (CDCl3, 400 MHz) δ 1.00-1.09 (m, 1H), 1.50-1.87 (m, 7H), 1.97-2.06 (m, 1H), 2.65-2.77 (m, 2H), 3.16-3.26 (m, 2H), 3.32 (s, 2H), 3.40 (d, J=13.3 Hz, 1H), 3.49 (d, J=13.3 Hz, 1H), 7.22-7.33 (m, 5H).

후처리

  1. temperatureAfter cooling to 0° C.
  2. stirringthe mixture was stirred at room temperature for another 3 hours
  3. extractionextracted with ethyl acetate (100 mL×3)
  4. washwashed with brine
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe obtained crude product
  9. customwas purified by column chromatography (SiO2, ethyl acetate/ethanol/triethylamine=80:15:5) to thereby provide 3-(aminomethyl)-1-(4-chlorobenzyl)piperidine (2.05 g, 55%)

출처 및 근거

ORD 기록
ord-dd0309bd0e32447b96a3603de101db20
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07390830B1

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