Piperidine → Phenylmethyl alpha-[[[2-(dimethylamino)ethyl]thio]methyl]benzenepropanoate

HRID 2186315

Reaktionsgleichung

Reaktionsgleichung von HRID 2186315
[CH2:1]=[C:2]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:3]([O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:4].Cl.[CH3:21][N:22]([CH3:26])[CH2:23][CH2:24][SH:25].N1CCCCC1.[OH-].C([N+](C)(C)C)C1C=CC=CC=1>CO>[CH3:21][N:22]([CH3:26])[CH2:23][CH2:24][S:25][CH2:1][CH:2]([CH2:13][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[C:3]([O:5][CH2:6][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1)=[O:4]

Komponenten

6

Edukt 4

HCID 8082PiperidineHCID 25798Captamine HydrochlorideHCID 66854Benzyltrimethylammonium hydroxideHCID 10912012Benzyl 2-Benzylacrylate

Produkt 1

HCID 15296671Phenylmethyl alpha-[[[2-(dimethylamino)ethyl]thio]methyl]benzenepropanoateAusbeute 24 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel2×

Versuchsvorschrift

The oil prepared in Step 9 (1.5 g, 5.95 mmol) was dissolved under argon in methanol (22 mL). To this solution was added 2-dimethylaminoethanethiol hydrochloride (843 mg, 5.95 mmol), piperidine (0.78 mL, 7.85 mmol) and benzyltrimethylammonium hydroxide (0.25 mL, 0.6 mmol), and the mixture was stirred at room temperature for 16 hours. The solvent was removed on a rotary evaporator and then the residue was purified by flash chromatography on silica gel, eluting with 20:1 CH2Cl2:MeOH to give the pure title compound (0.5 g, 24% yield). 1H NMR: 300 MHz spectrum consistent with proposed structure. Anal: calcd. for C21H27NO2S+0.2H2O: C, 69.85; H, 7.65; N, 3.88. Found: C, 69.58; H, 7.60; N, 3.98.

Aufarbeitung

  1. customThe solvent was removed on a rotary evaporator
  2. customthe residue was purified by flash chromatography on silica gel
  3. washeluting with 20:1 CH2Cl2

Quellen und Nachweise

ORD-Eintrag
ord-38a39fce53664b6394c68d98e2f32edd
Quelldatensatz
uspto-grants-2002_06
Patentnummer
US06403648B2

Verknüpfte Notizen

Wird geladen…