Propane sultone → 3-[(1-Methylcycloheptyl)amino]propane-1-sulfonic acid

HRID 239785Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 239785
[CH2:1]1[CH2:7][S:4](=[O:6])(=[O:5])[O:3][CH2:2]1.[CH3:8][C:9]1([NH2:16])[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1>C1(C)C=CC=CC=1>[CH3:8][C:9]1([NH:16][CH2:2][CH2:1][CH2:7][S:4]([OH:3])(=[O:6])=[O:5])[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1

Komponenten

4

Edukt 2

HCID 14264Propane sultoneHCID 145933331-Methylcycloheptan-1-amine

Produkt 1

HCID 160359453-[(1-Methylcycloheptyl)amino]propane-1-sulfonic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A solution of 1,3-propanesultone (4.3 g, 35 mmol) in toluene (10 mL) was added dropwise to a the crude solution of 1-methyl-1-cycloheptylamine in MTBK (total volume 30 mL). The mixture was heated to reflux for 18 hours then was cooled to room temperature. The solid was collected by suction filtration, rinsed with acetone (2×5 mL). The solid was dried overnight at 45° C. in the vacuum oven. The title compound was obtained as a fine white solid (7.77 g, 31.2 mmol, 80% overall yield). 1H NMR (500 MHz, D2O) δ 1.27 (s, 3H), 1.40-1.60 (m, 8H), 1.71-1.81 (m, 4H), 2.00-2.06 (m, 2H), 2.95 (t, J=6.3 Hz, 2H), 3.13 (t, J=7.1 Hz, 2H); 13C NMR (125 MHz, D2O) δ 22.0, 22.1, 23.3, 29.5, 37.1, 40.0, 48.3, 64.0; ES-MS 250(M+H)

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 18 hours
  3. filtrationThe solid was collected by suction filtration
  4. washrinsed with acetone (2×5 mL)
  5. customThe solid was dried overnight at 45° C. in the vacuum oven

Quellen und Nachweise

ORD-Eintrag
ord-0efdc8b39d5846808467cf1562290678
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08642801B2

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