3-Methoxypropylamine → 3-(4-bromophenyl)-N-(3-methoxypropyl)propan-1-amine

HRID 217785

Reaktionsgleichung

Reaktionsgleichung von HRID 217785
CS(O[CH2:6][CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([Br:15])=[CH:11][CH:10]=1)(=O)=O.[CH3:16][O:17][CH2:18][CH2:19][CH2:20][NH2:21].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Br:15][C:12]1[CH:13]=[CH:14][C:9]([CH2:8][CH2:7][CH2:6][NH:21][CH2:20][CH2:19][CH2:18][O:17][CH3:16])=[CH:10][CH:11]=1

Komponenten

5

Edukt 3

HCID 16723-MethoxypropylamineHCID 11430Potassium CarbonateHCID 196884663-(4-Bromophenyl)propyl methanesulphonate2×

Produkt 1

HCID 666785803-(4-bromophenyl)-N-(3-methoxypropyl)propan-1-amine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

3-(4-bromophenyl)propyl methanesulfonate (418 g) and acetonitrile (2 L) were charged into reactor 1. 3-methoxypropylamine (305 g) and potassium carbonate (394 g) were added to reactor 1 and the mixture was warmed to 80-90° C. for 4-16 h. The mixture was analysed for completion (3-(4-bromophenyl)propyl methanesulfonate <0.5%). The reaction was cooled to 25° C. and the suspension was filtered to remove the white solids. The filtrate was concentrated to dryness on a rotary evaporator. The crude product from the rotary evaporator, MTBE (2 L) and water (1.5 L) were charged into reactor 2. After phase separation, the organic layer was collected and washed with 1N HCl (2 L) until pH=4-5. After phase separation, the aqueous phase was basified by 2.5N NaOH solution to pH=9-10 and the resulting aqueous solution was used in the next step without further treatment.

Aufarbeitung

  1. temperatureThe reaction was cooled to 25° C.
  2. filtrationthe suspension was filtered
  3. customto remove the white solids
  4. concentrationThe filtrate was concentrated to dryness on a rotary evaporator
  5. customThe crude product from the rotary evaporator, MTBE (2 L) and water (1.5 L)
  6. additionwere charged into reactor 2
  7. customAfter phase separation
  8. customthe organic layer was collected
  9. washwashed with 1N HCl (2 L) until pH=4-5
  10. customAfter phase separation

Quellen und Nachweise

ORD-Eintrag
ord-a183de74b8264e66a58fed0d0b7f9435
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08198285B2

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