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Isobutylene → 3-Cyclohexyl-1-[4-[4-[2-(1,1-dimethylethoxy)phenyl]-1-piperidinyl]butan-1-yl]-2-imidazolidinone Oxalate

HRID 1057669
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1057669
[CH:1]1([N:7]2[CH2:11][CH2:10][N:9]([CH2:12][CH2:13][CH2:14][CH2:15][N:16]3[CH2:21][CH2:20][CH:19]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=4[OH:28])[CH2:18][CH2:17]3)[C:8]2=[O:29])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:30]([O:34][C:35](N1CCC(C2C=CC=CC=2O)CC1)=[O:36])([CH3:33])([CH3:32])[CH3:31].ClCCCCN1CCN(C2CCCCC2)[C:56]1=[O:66].CC(=C)C.FC(F)(F)S(O)(=O)=O>C(Cl)Cl.C(N(CC)CC)C>[C:56]([OH:66])(=[O:28])[C:35]([OH:36])=[O:34].[CH:1]1([N:7]2[CH2:11][CH2:10][N:9]([CH2:12][CH2:13][CH2:14][CH2:15][N:16]3[CH2:21][CH2:20][CH:19]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=4[O:28][C:30]([CH3:33])([CH3:32])[CH3:31])[CH2:18][CH2:17]3)[C:8]2=[O:29])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 5

HCID 8255IsobutyleneHCID 62406Trifluoromethanesulfonic acidHCID 17174861Tert-butyl 4-(2-hydroxyphenyl)piperidine-1-carboxylateHCID 186721001-(4-Chloro-1-butyl)-3-cyclohexyl-2-imidazolidinoneHCID 186721333-Cyclohexyl-1-[4-[4-(2-hydroxyphenyl)-1-piperidinyl]butan-1-yl]-2-imidazolidinone

Produkt 1

HCID 18672123
3-Cyclohexyl-1-[4-[4-[2-(1,1-dimethylethoxy)phenyl]-1-piperidinyl]butan-1-yl]-2-imidazolidinone Oxalate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8471TriethylamineLösungsmittel

Reaktionsbedingungen

Temperatur
-20 °C

Versuchsvorschrift

A solution of 3-cyclohexyl-1-[4-[4-(2-hydroxyphenyl)-1-piperidinyl]butan-1-yl]-2-imidazolidinone (1 g, prepared from 4-(2-hydroxyphenyl)piperidine (described in Example 5) and 1a by the method described in Example 4) in dry methylene chloride (10 ml) was cooled to −20° C. Isobutylene (5 ml, condensed at −25° C.) was added under a nitrogen atmosphere followed by addition of trifluoromethanesulfonic acid (0.4 ml). The mixture was stirred for 3 h at −20° C. followed by addition of triethylamine (2 mL). After warming to room temperature the reaction mixture was concentrated in vacuo followed by addition of 2 M ammonia and extraction with methylene chloride. The organic phase was dried over magnesium sulfate and concentrated in vacuo leaving an oil which was purified by flash chromatography (silica gel, eluent: ethyl acetate/MeOH/triethylamine 97:2:1). The resulting colorless oil was dissolved in a mixture of ethyl acetate and acetone. Addition of oxalic acid gave the title compound, 10a, as a crystalline material. Yield: 0.8 g, mp: 147-53° C. 1H NMR (DMSO-d6): δ 0.95-2.10 (m, 18H), 1.35 (s, 9H), 2.85-3.15 (m, 7H), 3.25 (s, 4H), 3.35-3.60 (m, 3H), 6.90-7.25 (m, 4H).

Aufarbeitung

  1. temperatureAfter warming to room temperature the reaction mixture
  2. concentrationwas concentrated in vacuo
  3. additionfollowed by addition of 2 M ammonia and extraction with methylene chloride
  4. dry with materialThe organic phase was dried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customleaving an oil which
  7. customwas purified by flash chromatography (silica gel, eluent: ethyl acetate/MeOH/triethylamine 97:2:1)
  8. dissolutionThe resulting colorless oil was dissolved in a mixture of ethyl acetate and acetone
  9. additionAddition of oxalic acid

Quellen und Nachweise

ORD-Eintrag
ord-b9faefed9e224b9a853644e6c19d17d8
Quelldatensatz
uspto-grants-2003_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06514993B1

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