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Hydrochloric Acid → 3-carboethoxy-3-[4-(3,4-dimethoxyphenyl)-4-isopropyl-4-cyanobutyl]-6,7-dimethoxy-N-methyl-1,2,3,4-tetrahydroisoquinoline

HRID 979367
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HRID 979367 반응식
[C:1]([CH:6]1[CH2:15][C:14]2[C:9](=[CH:10][C:11]([O:18][CH3:19])=[C:12]([O:16][CH3:17])[CH:13]=2)[CH2:8][N:7]1[CH3:20])([O:3][CH2:4][CH3:5])=[O:2].[Li+].CC([N-]C(C)C)C.[CH3:29][O:30][C:31]1[CH:32]=[C:33]([C:39]([CH:46]([CH3:48])[CH3:47])([CH2:42][CH2:43][CH2:44]I)[C:40]#[N:41])[CH:34]=[CH:35][C:36]=1[O:37][CH3:38].Cl>C1COCC1>[C:1]([C:6]1([CH2:44][CH2:43][CH2:42][C:39]([C:33]2[CH:34]=[CH:35][C:36]([O:37][CH3:38])=[C:31]([O:30][CH3:29])[CH:32]=2)([CH:46]([CH3:48])[CH3:47])[C:40]#[N:41])[CH2:15][C:14]2[C:9](=[CH:10][C:11]([O:18][CH3:19])=[C:12]([O:16][CH3:17])[CH:13]=2)[CH2:8][N:7]1[CH3:20])([O:3][CH2:4][CH3:5])=[O:2]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 2724682Lithium diisopropylamideHCID 140271622-(3,4-Dimethoxyphenyl)-2-isopropyl-2-(3-iodopropyl)acetonitrileHCID 202022163-carboethoxy-6,7-dimethoxy-N-methyl-1,2,3,4-tetrahydroisoquinoline

생성물 1

HCID 202022283-carboethoxy-3-[4-(3,4-dimethoxyphenyl)-4-isopropyl-4-cyanobutyl]-6,7-dimethoxy-N-methyl-1,2,3,4-tetrahydroisoquinoline

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
0 °C

실험 절차

The resulting ester of formula 31 is then treated with an iodoalkane of formula 22 (see Scheme III, step 2) in the presence of a strong base to form an alkylated tetrahydroisoquinoline ester of formula 32. For example, 3-carboethoxy-6,7-dimethoxy-N-methyl-1,2,3,4-tetrahydroisoquinoline (31) is added to a solution of LDA in THF at -70° C. and allowed to stand for 5-60 minutes, preferably about 10 minutes. To this reaction mixture is then added 2-(3,4-dimethoxyphenyl)-2-isopropyl-2-(3-iodopropyl)acetonitrile (22) in THF, and the resulting mixture allowed to warm to about 0° C. The mixture is then acidified, for example with dilute HCl, and the product extracted and purified to produce 3-carboethoxy-3-[4-(3,4-dimethoxyphenyl)-4-isopropyl-4-cyanobutyl]-6,7-dimethoxy-N-methyl-1,2,3,4-tetrahydroisoquinoline (32).

후처리

  1. extractionthe product extracted
  2. custompurified

출처 및 근거

ORD 기록
ord-1626a6cd0168476e84f3514f37a21788
출처 데이터셋
uspto-grants-1987_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04667038

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