Tributylphosphine → [3-(Benzo[b]thiophen-4-yloxy)-5-methyl-hexyl]-benzyl-methyl-amine

HRID 2220352Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2220352
N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O.[CH2:19]([N:26]([CH3:35])[CH2:27][CH2:28][CH:29]([OH:34])[CH2:30][CH:31]([CH3:33])[CH3:32])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.O[C:37]1[C:42]2[CH:43]=[CH:44][S:45][C:41]=2[CH:40]=[CH:39][CH:38]=1.C(P(CCCC)CCCC)CCC>ClCCl.C1(C)C=CC=CC=1>[S:45]1[CH:44]=[CH:43][C:42]2[C:37]([O:34][CH:29]([CH2:30][CH:31]([CH3:32])[CH3:33])[CH2:28][CH2:27][N:26]([CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH3:35])=[CH:38][CH:39]=[CH:40][C:41]1=2

Komponenten

7

Edukt 4

HCID 13831TributylphosphineHCID 19217Benzo(b)thiophen-4-olHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 179819191-(Benzyl-methyl-amino)-5-methyl-hexan-3-ol

Produkt 1

HCID 10316919[3-(Benzo[b]thiophen-4-yloxy)-5-methyl-hexyl]-benzyl-methyl-amineAusbeute 59,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Add 1,1′-(azodicarbonyl)dipiperidine (1.6901 g, 6.698 mmol) to a stirred solution of 1-(benzyl-methyl-amino)-5-methyl-hexan-3-ol (1.0463 g, 4.445 mmol), 4-hydroxybenzo-thiophene (1.0027 g, 6.676 mmol), tributylphosphine (1.70 mL, 6.82 mmol), and anhydrous toluene (15 mL). Heat the reaction to 70° C. under nitrogen for 18 hours. Cool the reaction to room temperature and dilute with dichloromethane. Filter off the solid material and concentrate the solvent off on a rotary evaporator to give the crude product. Purify the crude product by flash chromatography on silica gel eluting with 10% ethyl acetate /dichloromethane to yield 0.9674 g (59%) of [3-(benzo[b]thiophen-4-yloxy)-5-methyl-hexyl]-benzyl-methyl-amine: mass spectrum (ion spray) m/z=368.3(M+1); 1H NMR (CDCl3) δ 7.46-7.41 (m, 2H), 7.29-7.21 (m, 7H), 6.83 (d, 1H), 4.66-4.60 (m, 1H), 3.47 (s, 2H), 2.54-2.51 (m, 2H), 2.19 (s, 3H), 2.02-1.71 (m, 4H), 1.49-1.42 (m, 1H), 0.95 (d, 3H), 0.89 (d, 3H).

Aufarbeitung

  1. temperatureHeat
  2. customthe reaction to 70° C. under nitrogen for 18 hours
  3. temperatureCool
  4. customthe reaction to room temperature
  5. filtrationFilter off the solid material
  6. concentrationconcentrate the solvent
  7. customoff on a rotary evaporator
  8. customto give the crude product
  9. customPurify the crude product by flash chromatography on silica gel eluting with 10% ethyl acetate /dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-b6d4ccd097df439893e64707d686271e
Quelldatensatz
uspto-grants-2008_08
Patentnummer
US07417064B2

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