1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → (+)-4-Phenyl4-[(1-(3,5-bis(trifluoromethyl)phenyl)-2-hydroxyethoxy)methyl]-1-(2-(pyrrolidinyl)acetamido)piperidine Hydrochloride

HRID 962481

Reaktionsgleichung

Reaktionsgleichung von HRID 962481
[ClH:1].C[N:3](C)CCCN=C=NCC.O.O.O.OC1C2N=NNC=2C=CC=1.Cl.[N:27]1([CH2:32][C:33]([OH:35])=O)[CH2:31][CH2:30][CH2:29][CH2:28]1.Cl.[C:37]1([C:43]2([CH2:49][O:50][CH:51]([C:54]3[CH:59]=[C:58]([C:60]([F:63])([F:62])[F:61])[CH:57]=[C:56]([C:64]([F:67])([F:66])[F:65])[CH:55]=3)[CH2:52][OH:53])[CH2:48][CH2:47][NH:46][CH2:45][CH2:44]2)[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>CN(C)C=O.C(N(CC)CC)C>[ClH:1].[C:37]1([C:43]2([CH2:49][O:50][CH:51]([C:54]3[CH:59]=[C:58]([C:60]([F:61])([F:62])[F:63])[CH:57]=[C:56]([C:64]([F:67])([F:65])[F:66])[CH:55]=3)[CH2:52][OH:53])[CH2:48][CH2:47][N:46]([NH:3][C:33](=[O:35])[CH2:32][N:27]3[CH2:28][CH2:29][CH2:30][CH2:31]3)[CH2:45][CH2:44]2)[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1

Komponenten

7

Edukt 4

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 130220162-(Pyrrolidin-1-yl)acetic acid hydrochlorideHCID 190847004-Phenyl-4-((1-(3,5-bis(trifluoromethyl)phenyl)-2-hydroxyethoxy) methyl)piperidine HydrochlorideHCID 178526977HCID 178526977, Verbindung

Produkt 1

HCID 19084703(+)-4-Phenyl4-[(1-(3,5-bis(trifluoromethyl)phenyl)-2-hydroxyethoxy)methyl]-1-(2-(pyrrolidinyl)acetamido)piperidine Hydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittel2×HCID 8471TriethylamineLösungsmittel2×

Versuchsvorschrift

1-[3-Dimethylaminopropyl]-3-ethylcarbodiimide hydrochloride (797 mg), hydroxybenzo-triazole trihydrate (475 mg) and triethylamine (0.890 ml) were added to a stirred solution of 2-pyrrolidinyl acetic acid hydrochloride (528 mg) in dry dimethylformamide at room temperature. After 30 minutes a solution of the compound of Example 14 (800 mg) in dry dimethylformamide was added, followed by triethylamine (0.590 ml). The resulting solution was stirred at room temperature for 4 hours. The reaction was quenched with water and extracted into diethyl ether then the organic solution was dried (MgSO4) and evaporated to give a yellow oil. The residue was purified by chromatography on grade 3 neutral alumina (1% methanol/dichloromethane) then treated with ethereal hydrogen chloride to afford the title compound, mp=106°-108° C.;

Aufarbeitung

  1. customThe reaction was quenched with water
  2. extractionextracted into diethyl ether
  3. dry with materialthe organic solution was dried (MgSO4)
  4. customevaporated
  5. customto give a yellow oil
  6. customThe residue was purified by chromatography on grade 3 neutral alumina (1% methanol/dichloromethane)
  7. additionthen treated with ethereal hydrogen chloride

Quellen und Nachweise

ORD-Eintrag
ord-5faa7a865d2c4324a338648b88c1030b
Quelldatensatz
uspto-grants-1998_06
Patentnummer
US05760018

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