Benzylamine → HCID 10267702, compound

HRID 1860383Notes

Reaction equation

HRID 1860383 reaction equation
Cl[CH2:2][CH:3]1[CH2:7][CH2:6][CH:5]([CH2:8]Cl)[N:4]1[C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:23]([NH2:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>COCCOCCOC.C(OCC)C>[CH2:23]([N:30]1[CH2:8][CH:5]2[N:4]([C:10]3[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=3)[CH:3]([CH2:7][CH2:6]2)[CH2:2]1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

6

Reactant 3

HCID 7504BenzylamineHCID 11430Potassium CarbonateHCID 57440111HCID 57440111, compound

Product 1

HCID 10267702HCID 10267702, compoundYield 23.6%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8150DiglymeSolvent

Procedure

2,5-Bis-chloromethyl-1-(4-chlorophenyl)-pyrrolidine (3.73 g, 13.57 mmol), potassium carbonate (3.75 g, 27.14 mmol), and benzyl amine (4.45 mL, 40.71 mmol) in diglyme (25 mL) was heated at reflux for 15 h. The reaction mixture was cooled to room temperature, diluted with diethyl ether (600 mL) and washed with water (6×300 mL). The combined organic layers were dried with magnesium sulfate and concentrated to a brown oil. Silica gel flash chromatography using 50% chloroform/hexanes as eluent yielded 3-Benzyl-8-(4-chloro-phenyl)-3,8-diaza-bicyclo[3.2.1]octane (1.0 g, 23.5%) as a golden solid which had the following properties: Mp. 115-117° C.; 1H NMR CDCl3 δ: 7.29 (s, 5H), 7.14 (d, J=8.1 Hz, 2H), 6.67 (d, J=8.3 Hz, 2H), 4.08 (brd s, 2H), 3.38 (s, 2H), 2.54-2.42 (m, 4H), 2.08-2.00 (m, 2H), 1.95-1.86 (m,2H).

Workup

  1. temperatureat reflux for 15 h
  2. washwashed with water (6×300 mL)
  3. dry with materialThe combined organic layers were dried with magnesium sulfate
  4. concentrationconcentrated to a brown oil

Sources & evidence

ORD record
ord-399ba2bdfefe46419c88f30836263950
Source dataset
uspto-grants-2003_03
Patent number
US06531468B2

Reaction notes

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