Methanol → Methyl 6,7,8,9-tetrahydropyrido[1,2-a]indole-1-carboxylate

HRID 2082318

반응식

HRID 2082318 반응식
[CH:1]1[CH:9]=[CH:8][CH:7]=[C:6]2[C:2]=1[CH:3]=[C:4]1[CH2:13][CH2:12][CH2:11][CH2:10][N:5]12.[C:14](Cl)(Cl)=[O:15].[CH3:18][OH:19]>C(Cl)Cl.C1(C)C=CC=CC=1>[C:1]1([C:18]([O:15][CH3:14])=[O:19])[C:2]2[CH:3]=[C:4]3[CH2:13][CH2:12][CH2:11][CH2:10][N:5]3[C:6]=2[CH:7]=[CH:8][CH:9]=1

참가 물질

6

반응물 3

HCID 887MethanolHCID 6371PhosgeneHCID 108559426,7,8,9-Tetrahydropyrido[1,2-a]indole

생성물 1

HCID 19778122Methyl 6,7,8,9-tetrahydropyrido[1,2-a]indole-1-carboxylate수율 70.3%

시약·촉매·용매 2

HCID 1140Toluene용매HCID 6344Dichloromethane용매

실험 절차

6,7,8,9-tetrahydropyrido[1,2-a]indole (1.15 g, 6.7 mmol) in methylene chloride (5 ml) was added dropwise at 0° C. to a solution of phosgene (10 mmol) in toluene (5 ml). The reaction mixture was stirred for one hour after which methanol (1 ml) was added gradually and the mixture allowed to warm to ambient temperature. The solvent was removed under reduced pressure to yield a white solid. Recrystallization from hexane afforded 1.08 g (70.3% of methyl 6,7,8,9-tetrahydropyrido[1,2-a]indole-1-carboxylate, as white crystals, m.p. 102°-103° C. Anal. for C14H15NO2 : Calcd. C, 73.34; H, 6.59; N, 6.11. Found: C, 72.96; H, 6.61; N, 6.33.

후처리

  1. additionwas added gradually
  2. customThe solvent was removed under reduced pressure
  3. customto yield a white solid
  4. customRecrystallization from hexane

출처 및 근거

ORD 기록
ord-ba37bc30eb764beab3f6b6c46c68ea25
출처 데이터셋
uspto-grants-1993_02
특허 번호
US05189041

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