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

HRID 128250

Reaction equation

HRID 128250 reaction equation
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

Participants

8

Reactant 6

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

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 acetone 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.)

Workup

  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 acetone

Sources & evidence

ORD record
ord-c668c8b0a02e433fb1f7a626b94a052b
Source dataset
uspto-grants-1981_03
Patent number
US04259238

Linked notes

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