Trifluoroacetic acid → HCID 22913027, Verbindung

HRID 1968972Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1968972
[C:1]1([CH2:7][N:8]([CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:9]2[CH2:14][CH2:13][N:12](C(OC(C)(C)C)=O)[CH2:11][CH2:10]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(O)(C(F)(F)F)=O>ClCCl>[C:23]1([CH2:22][N:8]([CH2:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acid2×HCID 59444161HCID 59444161, Verbindung

Produkt 1

HCID 22913027HCID 22913027, VerbindungAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

1,1-Dimethylethyl 4-[bis(phenylmethyl)amino]-1-piperidinecarboxylate D74 (160 g, 420 mmol) was dissolved in dichloromethane (DCM) (1 L) and TFA (188 mL, 2443 mmol) was added dropwise at room temperature. The resulting mixture was stirred for 3 h then further 100 mL of TFA was added and stirred for 2 h. The mixture was concentrated under reduced pressure and the residue treated with saturated solution NaHCO3 (1.5 L) and NaOH (3M solution; 200 mL) to basic pH. The aqueous phase was extracted with DCM (2×1.5 L). Combined organic layers were diluted with ethyl acetate (100 mL), washed with water (1×1 L) and brine (1×1 L) then dried on Na2SO4 and concentrated to obtain title material (118 g; 100%).

Aufarbeitung

  1. stirringstirred for 2 h
  2. concentrationThe mixture was concentrated under reduced pressure
  3. additionthe residue treated with saturated solution NaHCO3 (1.5 L) and NaOH (3M solution; 200 mL) to basic pH
  4. extractionThe aqueous phase was extracted with DCM (2×1.5 L)
  5. additionCombined organic layers were diluted with ethyl acetate (100 mL)
  6. washwashed with water (1×1 L) and brine (1×1 L)
  7. customthen dried on Na2SO4
  8. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-3cfb99ae273645b1a5d3260112496a13
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08426443B2

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