1-(2-Chloroethyl)pyrrolidine → 4-Adamantoyloxy-N-methyl-N-(2-pyrrolidinoethyl)aniline Dihydrochloride Dihydrate

HRID 259358

Reaktionsgleichung

Reaktionsgleichung von HRID 259358
CNC1C=CC([O:9][C:10]23[CH2:19][CH:14]4[CH2:15][CH:16]([CH2:18][CH:12]([CH2:13]4)[CH2:11]2)[CH2:17]3)=CC=1.[Li]CCCC.[Cl:25]CCN1CCCC1.[OH2:33].O.[ClH:35].Cl.[C:37]12([O:47][C:48]3[CH:62]=[CH:61][C:51]([N:52]([CH3:60])[CH2:53][CH2:54][N:55]4[CH2:59][CH2:58][CH2:57][CH2:56]4)=[CH:50][CH:49]=3)CC3CC(CC(C3)C1)C2>CCCCC.C1C=CC=CC=1.C1COCC1.C1(C)C=CC=CC=1.CO>[OH2:9].[OH2:47].[ClH:25].[ClH:35].[C:10]12([C:37]([O:47][C:48]3[CH:62]=[CH:61][C:51]([N:52]([CH3:60])[CH2:53][CH2:54][N:55]4[CH2:59][CH2:58][CH2:57][CH2:56]4)=[CH:50][CH:49]=3)=[O:33])[CH2:19][CH:14]3[CH2:15][CH:16]([CH2:18][CH:12]([CH2:13]3)[CH2:11]1)[CH2:17]2

Komponenten

10

Edukt 4

HCID 816691-(2-Chloroethyl)pyrrolidineHCID 12510299N-Methyl-p-(1-adamantyloxy)anilineHCID 203421994-adamantyloxy-N-methyl-N-(2-pyrrolidinoethyl)aniline dihydrochloride dihydrateHCID 178418339Butyllithium

Produkt 1

HCID 705880674-Adamantoyloxy-N-methyl-N-(2-pyrrolidinoethyl)aniline Dihydrochloride Dihydrate

Reagenzien, Katalysatoren, Lösungsmittel 5

HCID 241BenzeneLösungsmittelHCID 887MethanolLösungsmittelHCID 1140TolueneLösungsmittelHCID 8003PentaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To an ice:MeOH cooled solution of 2.0 g. (0.0078 mole) of N-Methyl-p-(1-adamantyloxy)aniline in 20 ml. THF was added 4.75 ml. of 1.64N BuLi in pentane. A solution of a 1:1 mixture of toluene, and 1-chloro-2-pyrrolidino ethane (2.08 g.) in 20 ml. THF was then added and the mixture stirred at room temperature for 1 hour and at reflux for 18 hours. The solution was allowed to cool, diluted with C6H6 and washed with H2O and brine. The residue remaining when the organic fraction was taken to dryness was dissolved in CH2Cl2, treated with 10 ml. HCl saturated Et2O and taken to dryness. The residual solid was recrystallized from CH2Cl2 :CH3CN to yield 1.93 g. (55%) of 4-adamantyloxy-N-methyl-N-(2-pyrrolidinoethyl)aniline dihydrochloride dihydrate, m.p. 189°-190° (efervess).

Aufarbeitung

  1. temperatureat reflux for 18 hours
  2. temperatureto cool
  3. washwashed with H2O and brine
  4. dissolutionwas dissolved in CH2Cl2
  5. additiontreated with 10 ml
  6. customThe residual solid was recrystallized from CH2Cl2
  7. customCH3CN to yield 1.93 g

Quellen und Nachweise

ORD-Eintrag
ord-77d61c5ff56a4c22b27a5758b6298f8a
Quelldatensatz
uspto-grants-1977_07
Patentnummer
US04036977

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