Benzoic Acid → tert-Butyl 3-(benzoylamino)piperidine-1-carboxylate

HRID 1765632

Reaktionsgleichung

Reaktionsgleichung von HRID 1765632
[C:1]([OH:9])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.CN(C)CCCN=C=NCC.C1C=CC2N(O)N=NC=2C=1.[NH2:32][CH:33]1[CH2:38][CH2:37][CH2:36][N:35]([C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[CH2:34]1>CN(C=O)C.C(N(CC)CC)C>[C:1]([NH:32][CH:33]1[CH2:38][CH2:37][CH2:36][N:35]([C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[CH2:34]1)(=[O:9])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

7

Edukt 4

HCID 243Benzoic AcidHCID 757711-HydroxybenzotriazoleHCID 5458091-BOC-3-AminopiperidineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Produkt 1

HCID 22017033tert-Butyl 3-(benzoylamino)piperidine-1-carboxylateAusbeute 39,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittel2×HCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

A solution of benzoic acid (0.123 g) in DMF (5 ml) was treated with 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (0.231 g), HOBT (0.163 g) and triethylamine (0.56 ml) and stirred at room temperature for 1 h. A solution of 3-amino-1-N-Boc-piperidine (0.3 g) in DMF (1 ml) was then added and stirring continued for 18 h. The solution was concentrated under reduced pressure to give an oil which was partitioned between ethyl acetate and water. The separated organic extracts were washed with water, hydrochloric acid (2N), saturated sodium bicarbonate solution and brine, dried (over magnesium sulphate) and concentrated under reduced pressure to give the title compound (0.120 g) as a yellow solid.

Aufarbeitung

  1. stirringstirring
  2. waitcontinued for 18 h
  3. concentrationThe solution was concentrated under reduced pressure
  4. customto give an oil which
  5. customwas partitioned between ethyl acetate and water
  6. washThe separated organic extracts were washed with water, hydrochloric acid (2N), saturated sodium bicarbonate solution and brine
  7. dry with materialdried (over magnesium sulphate)
  8. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-b7c7d5c57fcf42109abf79a459c9fb32
Quelldatensatz
uspto-grants-2007_06
Patentnummer
US07226929B2

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