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Phenylacetic Acid → 4-Acetamido-4-phenyl-1-[2-[1-(3,4-dichlorophenyl)-2-(N-methyl-N-benzylcarbonylamino)ethoxy]ethyl]piperidine hydrochloride hemihydrate

HRID 1843
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1843
F[P-](F)(F)(F)(F)F.N1([O:17][P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.Cl.Cl.[C:30]([NH:33][C:34]1([C:55]2[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=2)[CH2:39][CH2:38][N:37]([CH2:40][CH2:41][O:42][CH:43]([C:47]2[CH:52]=[CH:51][C:50]([Cl:53])=[C:49]([Cl:54])[CH:48]=2)[CH2:44][NH:45][CH3:46])[CH2:36][CH2:35]1)(=[O:32])[CH3:31].[C:61]1([CH2:67][C:68]([OH:70])=[O:69])[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=1.CC[Cl:73]>C(Cl)Cl.C(N(CC)CC)C>[OH2:17].[ClH:53].[C:30]([NH:33][C:34]1([C:55]2[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=2)[CH2:35][CH2:36][N:37]([CH2:40][CH2:41][O:42][CH:43]([C:47]2[CH:52]=[CH:51][C:50]([Cl:53])=[C:49]([Cl:54])[CH:48]=2)[CH2:44][N:45]([CH3:46])[C:68]([CH2:67][C:61]2[CH:62]=[CH:63][CH:64]=[CH:65][CH:66]=2)=[O:70])[CH2:38][CH2:39]1)(=[O:32])[CH3:31].[C:30]([NH:33][C:34]1([C:55]2[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=2)[CH2:35][CH2:36][N:37]([CH2:40][CH2:41][O:42][CH:43]([C:47]2[CH:52]=[CH:51][C:50]([Cl:53])=[C:49]([Cl:54])[CH:48]=2)[CH2:44][N:45]([C:68]([CH2:67][C:61]2[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=2)=[O:69])[CH3:46])[CH2:38][CH2:39]1)(=[O:32])[CH3:31].[ClH:73]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 999Phenylacetic AcidHCID 6337ChloroethaneHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 196925004-Acetamido-4-phenyl-1-[2-[1-(3,4-dichlorophenyl)-2-(N-methylamino)ethoxy]ethyl]piperidine dihydrochloride

Produkt 1

HCID 131720562
4-Acetamido-4-phenyl-1-[2-[1-(3,4-dichlorophenyl)-2-(N-methyl-N-benzylcarbonylamino)ethoxy]ethyl]piperidine hydrochloride hemihydrate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittel2×HCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

0.46 ml of triethylamine and then 0.5 g of BOP are added to a mixture of 0.5 g of the compound obtained in EXAMPLE 11, step B), 0.127 g of phenylacetic acid and 10 ml of DCM. The resulting mixture is concentrated under vacuum and the residue is taken up with AcOEt, washed with water, with 1N NaOH solution and with saturated NaCl solution, dried over MgSO4 and concentrated under vacuum. The residue is chromatographed on silica gel H using DCM and then a DCM/MeOH mixture (94/6; v/v) as the eluent. The product obtained is taken up with DCM, acidified to pH 1 by the addition of hydrochloric ether and concentrated under vacuum to give 0.42 g of the expected hydrochloride after crystallization from iso ether. M.p.=125° C.

Aufarbeitung

  1. concentrationThe resulting mixture is concentrated under vacuum
  2. washwashed with water, with 1N NaOH solution and with saturated NaCl solution
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated under vacuum
  5. customThe residue is chromatographed on silica gel H
  6. customThe product obtained
  7. concentrationconcentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-b505007df247456aa881670aca334437
Quelldatensatz
uspto-grants-1998_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05726313

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