Toluene → N-[2-(1-methylpyrrolidin-2-yl)ethyl]caprylamide

HRID 497065

반응식

HRID 497065 반응식
[NH2:1][CH2:2][CH2:3][CH:4]1[CH2:8][CH2:7][CH2:6][N:5]1[CH3:9].C1(C)C=CC=CC=1.C([O:19][C:20](=O)[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])C.[OH-].[Na+]>C(OCC)(=O)C.O>[CH3:9][N:5]1[CH2:6][CH2:7][CH2:8][CH:4]1[CH2:3][CH2:2][NH:1][C:20](=[O:19])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]

참가 물질

7

반응물 4

HCID 1140TolueneHCID 7799Ethyl octanoateHCID 14798Sodium HydroxideHCID 983882-(2-Aminoethyl)-1-methylpyrrolidine

생성물 1

HCID 9899788N-[2-(1-methylpyrrolidin-2-yl)ethyl]caprylamide수율 74.5%

시약·촉매·용매 2

HCID 962Water용매HCID 8857Ethyl Acetate용매

실험 절차

Toluene (1.0 ml), dried using MS 4A, was mixed with 1.48 ml of a n-hexane solution of 15% Me3Al. With the mixture being cooled in an ice-methanol bath, 0.25 ml (1.16 mmols) of 2-(2-aminoethyl)-1-methylpyrrolidine was added dropwise over about 2 minutes. After stirring for 20 minutes, the temperature was raised to room temperature, and 0.5 ml of a toluene solution of 0.2 g (1.16 mmols) of caprylic acid ethyl ester was added dropwise over 1 minute. After stirring for 2 hours at 70° C., the mixture was cooled with ice, and 10 ml of 1N NaOH was added dropwise. The mixture was stirred for 10 minutes, and water and ethyl acetate were added. Then, the mixture was separated into respective layers, and the organic layer was washed twice with 20 ml of a saturated aqueous solution of sodium chloride. After this layer was dried over anhydrous magnesium sulfate, it was concentrated under reduced pressure on a 30° C. water bath to obtain the captioned compound (yield 0.22 g). This compound was subjected to silica gel column chromatography (mobile phase: CHCl3:MeOH (19:1→9:1)) for purification. NMR and mass spectrum confirmed the purified compound to have the following structure:

후처리

  1. dry with materialToluene (1.0 ml), dried
  2. additionwas mixed with 1.48 ml of a n-hexane solution of 15% Me3Al
  3. temperatureWith the mixture being cooled in an ice-methanol bath
  4. stirringAfter stirring for 2 hours at 70° C.
  5. additionwas added dropwise
  6. stirringThe mixture was stirred for 10 minutes
  7. customThen, the mixture was separated into respective layers
  8. washthe organic layer was washed twice with 20 ml of a saturated aqueous solution of sodium chloride
  9. dry with materialAfter this layer was dried over anhydrous magnesium sulfate, it
  10. concentrationwas concentrated under reduced pressure on a 30° C. water bath

출처 및 근거

ORD 기록
ord-b69df3b1618c4dad8dab15b02595d4a6
출처 데이터셋
uspto-grants-2005_09
특허 번호
US06949553B2

연결된 노트

불러오는 중…