Benzyl Alcohol → Benzyl 1,2,3,4-tetrahydroisoquinoline-3-carboxylate hydrochloride

HRID 67056

반응식

HRID 67056 반응식
[CH2:1]([OH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:12][CH:11]([C:19](O)=[O:20])[NH:10]1.[ClH:22]>CCOCC>[ClH:22].[CH2:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:12][CH:11]([C:19]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:20])[NH:10]1

참가 물질

5

반응물 3

HCID 244Benzyl AlcoholHCID 313Hydrochloric AcidHCID 954891,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid

생성물 1

HCID 20273210Benzyl 1,2,3,4-tetrahydroisoquinoline-3-carboxylate hydrochloride

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

반응 조건

온도
90 °C

실험 절차

Benzyl alcohol, 750 ml, was treated with 150 g of commercial polyphosphoric acid and warmed and stirred at 90° C. to obtain a homogeneous mixture. Solid 1,2,3,4-tetrahydro-3-isoquinolinecarboxylic acid (S-form) 165.2 g was added. The mixture was stirred 4 hours at 95°-105° C. and then allowed to stand at room temperature for 18 hours. A solution of 18.5 g gaseous hydrochloric acid in 2.5 l of anhydrous ether was added, and the product separated slowly on cooling overnight. Filtration gave the crude benzyl 1,2,3,4-tetrahydro-3-isoquinoline carboxylate hydrochloride. This was purified by recrystallization from ethanol twice to give material with mp 190.5°-191° C.; [α]D 23=-83.3° (1% 1:1 methanol/1 N hydrochloric acid).

후처리

  1. temperaturewarmed
  2. customto obtain a homogeneous mixture
  3. stirringThe mixture was stirred 4 hours at 95°-105° C.
  4. customthe product separated slowly
  5. temperatureon cooling overnight
  6. filtrationFiltration

출처 및 근거

ORD 기록
ord-d41cb35c3c15423083594c06b142ee98
출처 데이터셋
uspto-grants-1982_08
특허 번호
US04344949

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