Clonidine → 2-[N-(2,6-dichlorophenyl)-N-(2-methyl-1-butene-4-yl)-amino]2-imidazoline

HRID 1277417

Reaction equation

HRID 1277417 reaction equation
[CH:1]1[CH:6]=[C:5]([Cl:7])[C:4]([NH:8][C:9]2[NH:13][CH2:12][CH2:11][N:10]=2)=[C:3]([Cl:14])[CH:2]=1.Br[CH2:16][CH2:17][C:18]([CH3:20])=[CH2:19].C(N(CC)CC)C>C1(C)C=CC=CC=1>[Cl:14][C:3]1[CH:2]=[CH:1][CH:6]=[C:5]([Cl:7])[C:4]=1[N:8]([C:9]1[NH:10][CH2:11][CH2:12][N:13]=1)[CH2:16][CH2:17][C:18]([CH3:20])=[CH2:19]

Participants

5

Reactant 3

HCID 2803ClonidineHCID 8471TriethylamineHCID 5495854-Bromo-2-methylbut-1-ene

Product 1

HCID 234541072-[N-(2,6-dichlorophenyl)-N-(2-methyl-1-butene-4-yl)-amino]2-imidazoline

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 6.9 gm (0.03 mol) of clonidine, 5.6 gm of 4-bromo-2-methyl-1-butene, and 5 ml of triethylamine in 25 ml of toluene was heated for 24 hours at 120° C. After cooling, the solvent was decanted, and the residue remaining was dissolved in 1 N hydrochloric acid. After extraction with ether several times (the ethereal extracts were abandoned), the solution was extracted with ether in fractions at stepwisely rising pH values (alkalizing with 2 N sodium hydroxide solution). The thin-layer chromatographically uniform ether extracts were united and dried over MgSO4, and the ether was evaporated in vacuo.

Workup

  1. temperatureAfter cooling
  2. customthe solvent was decanted
  3. dissolutionthe residue remaining was dissolved in 1 N hydrochloric acid
  4. extractionAfter extraction with ether several times (the ethereal extracts
  5. extractionwas extracted with ether in fractions
  6. dry with materialdried over MgSO4
  7. customthe ether was evaporated in vacuo

Sources & evidence

ORD record
ord-3d87352bb14d48abb106dbb312628568
Source dataset
uspto-grants-1981_07
Patent number
US04277487

Linked notes

Loading…