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Formic Acid → 4-(4-Acetamido-4-phenylpiperidino)-2-(3,4-dichlorophenyl)-N-formyl-N-[3,5-bis(trifluoromethyl)benzyl]butylamine

HRID 3045
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 3045
[CH:1]([OH:3])=O.Cl.CN(C)CCCN=C=NCC.[C:16]([NH:19][C:20]1([C:54]2[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=2)[CH2:25][CH2:24][N:23]([CH:26]([CH2:39][C:40]2[CH:45]=[C:44]([C:46]([F:49])([F:48])[F:47])[CH:43]=[C:42]([C:50]([F:53])([F:52])[F:51])[CH:41]=2)[CH2:27][CH:28]([C:31]2[CH:36]=[CH:35][C:34]([Cl:37])=[C:33]([Cl:38])[CH:32]=2)[CH2:29][NH2:30])[CH2:22][CH2:21]1)(=[O:18])[CH3:17].CN1CCOCC1>ClCCl.Cl.O>[C:16]([NH:19][C:20]1([C:54]2[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=2)[CH2:21][CH2:22][N:23]([CH:26]([CH2:39][C:40]2[CH:41]=[C:42]([C:50]([F:51])([F:53])[F:52])[CH:43]=[C:44]([C:46]([F:47])([F:48])[F:49])[CH:45]=2)[CH2:27][CH:28]([C:31]2[CH:36]=[CH:35][C:34]([Cl:37])=[C:33]([Cl:38])[CH:32]=2)[CH2:29][NH:30][CH:1]=[O:3])[CH2:24][CH2:25]1)(=[O:18])[CH3:17]
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Komponenten

8

Edukt 4

HCID 284Formic AcidHCID 79724-MethylmorpholineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 570149314-(4-Acetamido-4-phenylpiperidino)-2-(3,4-dichlorophenyl)-N-[3,5-bis(trifluoromethyl)benzyl]butylamine

Produkt 1

HCID 86752339
4-(4-Acetamido-4-phenylpiperidino)-2-(3,4-dichlorophenyl)-N-formyl-N-[3,5-bis(trifluoromethyl)benzyl]butylamine

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 313Hydrochloric AcidLösungsmittelHCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel3×

Versuchsvorschrift

To a 0° C. solution of formic acid (0.09 mL) in dichloromethane (3 mL) was added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.23 g) and the mixture stirred for 15 minutes. To this mixture was added a solution of 4-(4-acetamido-4-phenylpiperidino)-2-(3,4-dichlorophenyl)-N-[3,5-bis(trifluoromethyl)benzyl]butyl amine (0.40) and N-methylmorpholine (0.13 mL) in dichloromethane (5 mL). The mixture was allowed to warm to room temperature overnight, and was diluted with 1N hydrochloric acid (5 mL), dichloromethane, and water (5 mL). The layers were separated and the the aqueous phase was extracted with dichloromethane (10 mL). The combined organic layers were washed (brine), dried, and evaporated to afford material which was purified by chromatography with dichloromethane:methanol (20:1) as eluent, to give a hydrate of the title compound (0.206 g); mp 108°-110° C.; NMR: 8.1-7.5 (m,6), 7.3 (m,6), 4.75-4.40 (m,2), 3.75-3.3 (m,4), 3.3-3.0 (m,4), 2.85 (m,1), 1.95 (s,3), 2.25-1.80 (m,4); MS: m/z=688(M+1,100%); TLC: Rf =0.46 (10:1 dichloromethane:methanol). Analysis for C33H33Cl2F6N3O2.1.50 H2O: Calculated: C, 55.39; H, 5.07; N, 5.87; Found: C, 55.38; H, 4.77; N, 5.84.

Aufarbeitung

  1. customThe layers were separated
  2. extractionthe the aqueous phase was extracted with dichloromethane (10 mL)
  3. washThe combined organic layers were washed (brine)
  4. customdried
  5. customevaporated
  6. customto afford material which
  7. customwas purified by chromatography with dichloromethane:methanol (20:1) as eluent

Quellen und Nachweise

ORD-Eintrag
ord-0f557f1000674f4b902d975b3b805985
Quelldatensatz
uspto-grants-1998_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05731309

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