Diethyl Ether → 2-[[2-Methyl-4-((3-hydroxypropyloxy)carbonylamino)phenyl]amino]-1-pyrroline, hydrochloride

HRID 484799Notes

Reaction equation

HRID 484799 reaction equation
[ClH:1].Cl.[CH3:3][C:4]1[CH:9]=[C:8]([NH2:10])[CH:7]=[CH:6][C:5]=1[NH:11][C:12]1[CH2:16][CH2:15][CH2:14][N:13]=1.[CH2:17]([OH:21])[CH2:18][CH2:19][OH:20].[CH2:22]([O:24]CC)C>>[ClH:1].[CH3:3][C:4]1[CH:9]=[C:8]([NH:10][C:22]([O:20][CH2:19][CH2:18][CH2:17][OH:21])=[O:24])[CH:7]=[CH:6][C:5]=1[NH:11][C:12]1[CH2:16][CH2:15][CH2:14][N:13]=1

Participants

4

Reactant 3

HCID 3283Diethyl EtherHCID 104421,3-PropanediolHCID 1317142942-[(2-Methyl-4-aminophenyl)amino]-1-pyrroline, dihydrochloride

Product 1

HCID 704652542-[[2-Methyl-4-((3-hydroxypropyloxy)carbonylamino)phenyl]amino]-1-pyrroline, hydrochloride

Procedure

The title compound was prepared by the general method of Example 25 using the product compound of Example 9 and 1,3-propanediol. The reaction mixture was treated with an eight-fold quantity of diethyl ether, in which the product was not soluble. The oily product was triturated with several portions of ether until solid. The crude solid was stirred as a suspension in a small amount of 1:1 ethanol/methanol, and then collected by filtration. Drying in a high vacuum over 5A molecular sieves produced the desired compound as the hydrochloride salt.

Workup

  1. customThe oily product was triturated with several portions of ether until solid
  2. filtrationcollected by filtration
  3. dry with materialDrying in a high vacuum over 5A molecular sieves

Sources & evidence

ORD record
ord-329014683aca4a8493d2bd09dd52505a
Source dataset
uspto-grants-1985_08
Patent number
US04533739

Reaction notes

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