Trifluoroacetic acid → (7-Nitro-1,2,3,4-tetrahydro-naphthalen-2-yl)-piperidin-4-ylmethyl-propyl-amine

HRID 1168873Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1168873
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][N:15]([CH:19]2[CH2:28][CH2:27][C:26]3[C:21](=[CH:22][C:23]([N+:29]([O-:31])=[O:30])=[CH:24][CH:25]=3)[CH2:20]2)[CH2:16][CH2:17][CH3:18])[CH2:10][CH2:9]1)=O)(C)(C)C.C(NC(N1CCC(CN(CC)C2CCC3C(=CC(NC(=O)C4C=CC(S(C)(=O)=O)=CC=4)=CC=3)C2)CC1)=O)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[N+:29]([C:23]1[CH:22]=[C:21]2[C:26]([CH2:27][CH2:28][CH:19]([N:15]([CH2:14][CH:11]3[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]3)[CH2:16][CH2:17][CH3:18])[CH2:20]2)=[CH:25][CH:24]=1)([O-:31])=[O:30]

Komponenten

5

Edukt 3

HCID 6422Trifluoroacetic acidHCID 113074364-({Ethyl-[7-(4-methanesulfonyl-benzoylamino)-1,2,3,4-tetrahydro-naphthalen-2-yl]-amino}-methyl)-piperidine-1-carboxylic acid isopropylamideHCID 686245334-{[(7-Nitro-1,2,3,4-tetrahydro-naphthalen-2-yl)-propyl-amino]-methyl}-piperidine-1-carboxylic acid tert-butyl ester

Produkt 1

HCID 22560628(7-Nitro-1,2,3,4-tetrahydro-naphthalen-2-yl)-piperidin-4-ylmethyl-propyl-amine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 4-{[(7-nitro-1,2,3,4-tetrahydro-naphthalen-2-yl)-propyl-amino]-methyl}-piperidine-1-carboxylic acid tert-butyl ester, prepared as in Example 1 (1.12 g, 2.60 mmol) in methylene chloride (30 mL) under a nitrogen atmosphere was added trifluoroacetic acid (10 mL). The reaction was stirred at room temperature for 30 min. and concentrated in vacuo. The residue was partitioned between EtOAc (50 mL) and 10% aq. KOH (50 mL). The organic layer was separated, dried over MgSO4, filtered, and concentrated to afford (7-nitro-1,2,3,4-tetrahydro-naphthalen-2-yl)-piperidin-4-ylmethyl-propyl-amine (845 mg).

Aufarbeitung

  1. concentrationconcentrated in vacuo
  2. customThe residue was partitioned between EtOAc (50 mL) and 10% aq. KOH (50 mL)
  3. customThe organic layer was separated
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-0150f45257724bd185f4fb02a28b479e
Quelldatensatz
uspto-grants-2003_09
Patentnummer
US06627644B2

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