Potassium Hydroxide → 1H-Indol-5-amine, 3-(1,2,3,6-tetrahydro-1-methyl-4-pyridinyl)-

HRID 725961노트

반응식

HRID 725961 반응식
[OH-].[K+].[NH2:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[CH:7]2.[CH3:13][N:14]1[CH2:19][CH2:18][C:17](=O)[CH2:16][CH2:15]1>CO.O>[NH2:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[C:7]2[C:17]1[CH2:18][CH2:19][N:14]([CH3:13])[CH2:15][CH:16]=1

참가 물질

6

반응물 3

HCID 14797Potassium HydroxideHCID 740491-Methyl-4-piperidoneHCID 788675-Aminoindole

생성물 1

HCID 111488671H-Indol-5-amine, 3-(1,2,3,6-tetrahydro-1-methyl-4-pyridinyl)-수율 48.9%

시약·촉매·용매 2

HCID 887Methanol용매HCID 962Water용매

실험 절차

To a solution of 1.29 gm (20 mMol) potassium hydroxide in 10 mL methanol were added 1.32 gm (10 mMol) 5-amino-1H-indole followed by 2.46 mL (20 mMol) 1-methyl-4-piperidone. The reaction mixture was then heated to reflux for 18 hours. The reaction mixture was cooled to ambient, diluted with 20 ml water and the precipitate collected by filtration. The solid was recrystallized from ethyl acetate:methanol to give 1.11 gm (48.9%) 5-amino-3-(1-methyl-1,2,3,6-tetrahydropyr-idin-4-yl)-1H-indole as a tan solid (m.p.=200°-203° C.). The tan solid was subjected to flash chromatography, eluting with 100:20:0.5 dichloromethane:methanol:ammonium hydroxide, to give 0.99 gm 5-amino-3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indole as a cream colored solid (m.p.=212°-215° C. (ethyl acetate:methanol)).

후처리

  1. temperatureThe reaction mixture was then heated
  2. temperatureto reflux for 18 hours
  3. temperatureThe reaction mixture was cooled to ambient,
  4. filtrationthe precipitate collected by filtration
  5. customThe solid was recrystallized from ethyl acetate

출처 및 근거

ORD 기록
ord-b52587e371504faa819d3272ec2541ab
출처 데이터셋
uspto-grants-1998_01
특허 번호
US05708008

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