1,1-Dichloroethane → 3-[[N-(5,5-dimethyl-1-pyrrolin-2-yl)-p-anisidino]methyl]indole hydrochloride

HRID 1758349

반응식

HRID 1758349 반응식
P(Cl)(Cl)([Cl:3])=O.[CH3:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([NH:14][CH2:15][C:16]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[NH:18][CH:17]=2)=[CH:10][CH:9]=1.[CH3:25][C:26]1([CH3:32])[NH:30][C:29](=O)[CH2:28][CH2:27]1.C(N(CC)CC)C.ClC(Cl)C.[OH-].[Na+]>ClCCCl>[ClH:3].[CH3:25][C:26]1([CH3:32])[N:30]=[C:29]([N:14]([CH2:15][C:16]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[NH:18][CH:17]=2)[C:11]2[CH:12]=[CH:13][C:8]([O:7][CH3:6])=[CH:9][CH:10]=2)[CH2:28][CH2:27]1

참가 물질

8

반응물 6

HCID 63651,1-DichloroethaneHCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 918780N-((1H-indol-3-yl)methyl)-4-methoxyanilineHCID 111262105,5-dimethylpyrrolidin-2-one

생성물 1

HCID 205097773-[[N-(5,5-dimethyl-1-pyrrolin-2-yl)-p-anisidino]methyl]indole hydrochloride수율 19.8%

시약·촉매·용매 1

HCID 111,2-Dichloroethane용매

실험 절차

Phosphorus oxychloride (1.53 g., 0.01 mole), 3-(p-anisidinomethyl)indole, (2.52 g., 0.01 mole), 5,5-dimethyl-2-pyrrolidinone (1.13 g., 0.01 mole), and triethylamine (1.01 g., 0.01 mole) in 50 ml. of 1,2-dichloroethane is reacted according to the procedure of Example 36. After standing for 6 hr. at ice bath temperature, the reaction mixture is filtered affording the crude hydrochloride salt (1.45 g.) of the product, m.p. 188°-191° C. The dichloroethane filtrate is made basic with 10% sodium hydroxide, separated, dried over magnesium sulfate, acidified with ethanolic hydrogen chloride, and concentrated under reduced pressure. Trituration of the residue thus obtained with aceton yields a second crop of the hydrochloride, (0.76 g.), m.p. 191°-194° C. The hydrochloride fractions are combined and converted to the free base (m.p. 83°-85° C.) in the usual manner by dissolving in water and making basic with sodium hydroxide followed by extraction with ether. The hydrochloride salt is reprepared by taking the free base up in ethanol and acidifying with ethanolic hydrogen chloride to provide analytically pure 3-[[N-(5,5-dimethyl-1-pyrrolin-2-yl)-p-anisidino]methyl]indole hydrochloride, m.p. 188.5°-190.5° C. (dec.) (corr.)

후처리

  1. filtrationat ice bath temperature, the reaction mixture is filtered
  2. customaffording the crude hydrochloride salt (1.45 g.) of the product, m.p. 188°-191° C
  3. customseparated
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customTrituration of the residue thus obtained with aceton

출처 및 근거

ORD 기록
ord-32b4cbd782db42498cbc6af6c8a8a8db
출처 데이터셋
uspto-grants-1983_02
특허 번호
US04372887

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