Carbon Disulfide → [3-[3-(1-Piperidinylmethyl)phenoxy]propyl]isothiocyanate

HRID 325713

반응식

HRID 325713 반응식
[C:1](=[S:3])=S.[N:4]1([CH2:10][C:11]2[CH:12]=[C:13]([CH:19]=[CH:20][CH:21]=2)[O:14][CH:15](N)[CH2:16][CH3:17])[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1.C([N:24](CC)CC)C>CC(C)=O.[Hg](Cl)Cl>[N:4]1([CH2:10][C:11]2[CH:12]=[C:13]([CH:19]=[CH:20][CH:21]=2)[O:14][CH2:15][CH2:16][CH2:17][N:24]=[C:1]=[S:3])[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1

참가 물질

6

반응물 3

HCID 6348Carbon DisulfideHCID 8471TriethylamineHCID 212975763-(1-Piperidinylmethyl)phenoxy propanamine

생성물 1

HCID 13391620[3-[3-(1-Piperidinylmethyl)phenoxy]propyl]isothiocyanate

시약·촉매·용매 2

HCID 24085Mercuric Chloride촉매HCID 180Acetone용매3회

반응 조건

온도
-14 °C

실험 절차

A solution of carbon disulphide (3.3 ml) in acetone (8 ml) was added dropwise to a solution of 3-[3-(1-piperidinylmethyl)phenoxy propanamine (12.4 g) in acetone (30 ml) over a 15 minute period, between -5° and -10° C. The solution was cooled to -14° C. and mercury (II) chloride (13.6 g) in acetone (30 ml) was added, during 45 minutes. Triethylamine (16 ml) was added at 0° C. during 15 minutes, and the mixture was heated at reflux for 45 minutes. The resulting suspension was purified by filtration and the filtrate evaporated in vacuo. The residue was purified by column chromatography using methanol as eluant to give the title compound (6 g) as an amber oil.

후처리

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 45 minutes
  3. filtrationThe resulting suspension was purified by filtration
  4. customthe filtrate evaporated in vacuo
  5. customThe residue was purified by column chromatography

출처 및 근거

ORD 기록
ord-7e9628edab16419cb23c7252de072493
출처 데이터셋
uspto-grants-1984_04
특허 번호
US04442110

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