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Sodium Carbonate → trans-3-hydroxy-N,N,gamma-trimethyl-alpha,alpha-diphenyl-4-[[3-(trifluoromethyl)benzoyl]amino]-1-piperidinebutanamide

HRID 981308
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 981308
[NH2:1][C@@H:2]1[CH2:7][CH2:6][N:5]([CH:8]([CH3:28])[CH2:9][C:10]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:11]([N:13]([CH3:15])[CH3:14])=[O:12])[CH2:4][C@H:3]1[OH:29].[F:30][C:31]([F:42])([F:41])[C:32]1[CH:33]=[C:34]([CH:38]=[CH:39][CH:40]=1)[C:35](Cl)=[O:36].C(=O)([O-])[O-].[Na+].[Na+]>O.ClC(Cl)Cl.C(N(CC)CC)C>[OH:29][C@H:3]1[C@H:2]([NH:1][C:35](=[O:36])[C:34]2[CH:38]=[CH:39][CH:40]=[C:32]([C:31]([F:30])([F:41])[F:42])[CH:33]=2)[CH2:7][CH2:6][N:5]([CH:8]([CH3:28])[CH2:9][C:10]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:11]([N:13]([CH3:15])[CH3:14])=[O:12])[CH2:4]1
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Komponenten

7

Edukt 3

HCID 10340Sodium CarbonateHCID 752573-(Trifluoromethyl)benzoyl chlorideHCID 67928771trans-4-amino-3-hydroxy-N,N,gamma-trimethyl-alpha,alpha-diphenyl-1-piperidinebutanamide

Produkt 1

HCID 67928763trans-3-hydroxy-N,N,gamma-trimethyl-alpha,alpha-diphenyl-4-[[3-(trifluoromethyl)benzoyl]amino]-1-piperidinebutanamideAusbeute 86,3 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittel
HCID 6212ChloroformLösungsmittel2×
HCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

To a stirred and cooled solution of 4 parts of trans-4-amino-3-hydroxy-N,N,γ-trimethyl-α,αdiphenyl-1-piperidinebutanamide in 120 parts of trichloromethane were added 1.26 parts of N,N-diethylethanamine. A solution of 2.3 parts of 3-(trifluoromethyl)benzoyl chloride in 75 parts of trichloromethane was added dropwise. Upon completion, the reaction mixture was stirred overnight at room temperature. A solution of sodium carbonate in water was added. The separated organic layer was washed with water, dried, filtered and evaporated. The residue was taken up in 2,2'-oxybispropane. The precipitated product was filtered off and dried in vacuo at 60° C., yielding 4.9 parts (86.3%) of trans-3-hydroxy-N,N,γ-trimethyl-α,α-diphenyl-4-[[3-(trifluoromethyl)benzoyl]amino]-1-piperidinebutanamide; mp. 140.7° C. (compound 1).

Aufarbeitung

  1. stirringUpon completion, the reaction mixture was stirred overnight at room temperature
  2. washThe separated organic layer was washed with water
  3. customdried
  4. filtrationfiltered
  5. customevaporated
  6. filtrationThe precipitated product was filtered off
  7. customdried in vacuo at 60° C.

Quellen und Nachweise

ORD-Eintrag
ord-e573f253a5484472bf368ef0e328604a
Quelldatensatz
uspto-grants-1991_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04990521

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