Diisopropylethylamine → HCID 70454392, compound

HRID 365192Notes

Reaction equation

HRID 365192 reaction equation
Cl[C:2]1[N:3]([CH3:17])[C:4](=[O:16])[N:5]([CH3:15])[C:6](=[O:14])[C:7]=1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[O:18]([CH2:25][CH:26]([OH:32])[CH2:27][NH:28][CH2:29][CH2:30][NH2:31])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(N(C(C)C)C(C)C)C.[C:42](O)(=[O:48])/[CH:43]=[CH:44]/[C:45]([OH:47])=[O:46]>C(O)C.C(OCC)(=O)C.C(#N)C>[C:45]([OH:47])(=[O:46])/[CH:44]=[CH:43]/[C:42]([O:32][CH:26]([CH2:27][NH:28][CH2:29][CH2:30][NH:31][C:2]1[N:3]([CH3:17])[C:4](=[O:16])[N:5]([CH3:15])[C:6](=[O:14])[C:7]=1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH2:25][O:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:48]

Participants

8

Reactant 4

HCID 81531DiisopropylethylamineHCID 444972Fumaric AcidHCID 2784948AC1MD7HPHCID 145507661-[(2-Aminoethyl)amino]-3-phenoxypropan-2-ol

Product 1

HCID 70454392HCID 70454392, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

5.0 g. 4-Chloro-1,3-dimethyl-5-phenylpyrimidine-2,6(1H,3H)-dione, 4.2 g. 1-phenoxy-3-(2-aminoethylamino)-propan-2-ol and 3.5 ml. N-ethyldiisopropylamine are heated under reflux for 48 hours in 20 ml. acetonitrile. The reaction mixture is then evaporated, the residue is taken up in methylene chloride and the solution is shaken with 2N aqueous sodium hydroxide solution, dried and separated by column chromatography on silica gel using, as elution agent, methylene chloride-methanol-ammonia-saturated methanol (40:1:1 v/v/v). The oil (5.3 g.) obtained by evaporation of the pure fractions is dissolved in 10 ml. ethyl acetate, whereupon the solution is mixed with a solution of 2 g. fumaric acid in 20 ml. ethanol. After crystallization has taken place, the crystals are filtered off with suction and subsequently washed with ethyl acetate. There are obtained 6.7 g. (62% of theory) of the desired product in the form of colorless crystals; m.p. 181°-183° C.

Workup

  1. temperatureunder reflux for 48 hours in 20 ml
  2. customThe reaction mixture is then evaporated
  3. customdried
  4. customseparated by column chromatography on silica gel using, as elution agent, methylene chloride-methanol-ammonia-saturated methanol (40:1:1 v/v/v)
  5. customThe oil (5.3 g.) obtained by evaporation of the pure fractions
  6. dissolutionis dissolved in 10 ml
  7. customAfter crystallization
  8. filtrationthe crystals are filtered off with suction
  9. washsubsequently washed with ethyl acetate
  10. customThere are obtained 6.7 g

Sources & evidence

ORD record
ord-f125116deec7444697ccf63853966d18
Source dataset
uspto-grants-1986_08
Patent number
US04608383

Reaction notes

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