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

HRID 1758346

Reaction equation

HRID 1758346 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][CH:26]1[NH:30][C:29](=O)[CH2:28][CH2:27]1.C(N(CC)CC)C>ClCCCl>[ClH:3].[CH3:25][CH:26]1[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

6

Reactant 4

HCID 8471TriethylamineHCID 24813Phosphorus oxychlorideHCID 660555-Methyl-2-pyrrolidoneHCID 918780N-((1H-indol-3-yl)methyl)-4-methoxyaniline

Product 1

HCID 205097783-[[N-(5-methyl-1-pyrrolin-2-yl)-p-anisidino]methyl]indole hydrochloride

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Phosphorus oxychloride (3.06 g., 0.02 mole) in 10 ml. of 1,2-dichloroethane is added dropwise in 20 min. to a solution of 3-(p-anisidinomethyl)indole (5.04 g., 0.02 mole), 5-methyl-2-pyrrolidinone (1.98 g., 0.02 mole) and triethylamine (2.02 g., 0.02 mole) held at a temperature of about 3° C. When the addition is complete, the mixture is stirred at 3° to 4° C. for 5 hr. and then filtered to provide 2.4 g. solid which is crystallized from water affording 1.02 g., m.p. 184°-187° C. This fraction is combined with an additional 1.81 g. fraction obtained as hereinabove described and crystallized from ethanol to furnish analytically pure 3-[[N-(5-methyl-1-pyrrolin-2-yl)-p-anisidino]methyl]indole hydrochloride, m.p. 181.5°-183.5° C. (corr.)

Workup

  1. customheld at a temperature of about 3° C
  2. additionWhen the addition
  3. filtrationand then filtered
  4. customto provide 2.4 g
  5. customsolid which is crystallized from water affording 1.02 g
  6. customfraction obtained as hereinabove
  7. customcrystallized from ethanol

Sources & evidence

ORD record
ord-c5d9bab48c8044bf999cdbcb7fbae53c
Source dataset
uspto-grants-1983_02
Patent number
US04372887

Linked notes

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