Hydrochloric Acid → tert-butyl N-{3-[(3-aminopropyl)(methyl)amino]propyl}carbamate

HRID 615570

Reaktionsgleichung

Reaktionsgleichung von HRID 615570
O.[NH2:2][CH2:3][CH2:4][CH2:5][N:6]([CH2:8][CH2:9][CH2:10][NH2:11])[CH3:7].CC1C=C(C)N=C(S[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])N=1.Cl>O1CCOCC1.C(N(CC)CC)C>[C:24]([O:23][C:21]([NH:2][CH2:3][CH2:4][CH2:5][N:6]([CH2:8][CH2:9][CH2:10][NH2:11])[CH3:7])=[O:22])([CH3:27])([CH3:26])[CH3:25]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 7777N,N-bis(3-aminopropyl)methylamineHCID 148428O-(1,1-Dimethylethyl) S-(4,6-dimethyl-2-pyrimidinyl) carbonothioate

Produkt 1

HCID 12983660tert-butyl N-{3-[(3-aminopropyl)(methyl)amino]propyl}carbamateAusbeute 70,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8471TriethylamineLösungsmittel2×HCID 312751,4-DioxaneLösungsmittel2×

Versuchsvorschrift

Into 180 ml of water, was dissolved 150 g of bis(3-aminopropyl)methylamine followed by 53 g of triethylamine. To the solution, while being cooled in ice and stirred, was added portionwise a solution of 83 g (1/3 equivalent) of 4,6-dimethyl-2-tert-butoxycarbonylthiopyrimidine in 200 ml of dioxane. The mixture was allowed to react at room temperature for 5 hours. The reaction mixture was stripped of the dioxane and triethyl amine by disillation under reduced pressure. The residue was adjusted to pH 2 with 6N hydrochloric acid and washed with chloroform. The aquoues layer was adjusted to pH 13.5 with sodium hydroxide and extracted with chloroform. The chloroform layer was dried over sodium sulfate and freed from the solvent by distillation under reduced pressure to yield 60 g (24% yield) of (3-tert-butoxycarbonylaminopropyl)-(3-aminopropyl)methylamine (BOC-APMP).

Aufarbeitung

  1. temperatureTo the solution, while being cooled in ice
  2. customto react at room temperature for 5 hours
  3. washwashed with chloroform
  4. extractionextracted with chloroform
  5. dry with materialThe chloroform layer was dried over sodium sulfate
  6. distillationfreed from the solvent by distillation under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-d4222fa452ae4fcd82b9c1b4812f7090
Quelldatensatz
uspto-grants-1985_02
Patentnummer
US04500452

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