Dichloromethane → HCID 23045625, Verbindung

HRID 2108203Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2108203
Br.[CH2:2]([N:5]1[CH2:10][CH2:9][CH2:8][CH:7]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([OH:17])[CH:12]=2)[CH2:6]1)[CH2:3][CH3:4].[C:18]1([N:24]=[C:25]=[O:26])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(N(CC)CC)C.C(Cl)[Cl:35]>CO>[ClH:35].[CH2:2]([N:5]1[CH2:10][CH2:9][CH2:8][CH:7]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([O:17][C:25](=[O:26])[NH:24][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH:12]=2)[CH2:6]1)[CH2:3][CH3:4]

Komponenten

6

Edukt 4

HCID 6344DichloromethaneHCID 7672Phenyl isocyanateHCID 8471TriethylamineHCID 2304564779412-27-4

Produkt 1

HCID 23045625HCID 23045625, VerbindungAusbeute 20 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A mixture of N-n-propyl-3-(3-hydroxyphenyl)piperidine hydrobromide (0.76 g, 0.0025 mol), phenylisocyanate (5.45 g, 0.046 mol), triethylamine (0.5 g, 0.049 mol) and methylene chloride (2 ml) was stirred at r.t. for 18 h. The mixture was partitioned between water and ether. The ether phase was dried and evaporated giving a partly crystalline residue. The residue was dissolved in methanol and chromatographed on a silica gel column (200 g, SiO2) with methanol as eluant. The fractions which according to GLC contained the desired product in pure form were continued and the solvent evaporated. The residue was dissolved in ether and treated with HCl-saturated ether giving a crystalline precipitate. Filtration and washing gave 0.18 g (20%) of the desired hydrochloride, mp. 184°-190° C.

Aufarbeitung

  1. customThe mixture was partitioned between water and ether
  2. dry with materialThe ether phase was dried
  3. customevaporated
  4. customgiving a partly crystalline residue
  5. customchromatographed on a silica gel column (200 g, SiO2) with methanol as eluant
  6. customthe solvent evaporated
  7. dissolutionThe residue was dissolved in ether
  8. additiontreated with HCl-saturated ether giving a crystalline precipitate
  9. filtrationFiltration
  10. washwashing

Quellen und Nachweise

ORD-Eintrag
ord-e84c752363b843e08f2a2612036e4d82
Quelldatensatz
uspto-grants-1990_06
Patentnummer
US04937346

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