Potassium Carbonate → 12-(2-Methoxy-ethyl)-12-aza-tricyclo[7.2.1.0(2,7)]dodeca-2(7),3,5-trien-4-ylamine

HRID 1040619Notes

Reaction equation

HRID 1040619 reaction equation
[CH:1]12[NH:12][CH:9]([CH2:10][CH2:11]1)[CH2:8][C:7]1[CH:6]=[CH:5][C:4]([NH2:13])=[CH:3][C:2]2=1.Br[CH2:15][CH2:16][O:17][CH3:18].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:18][O:17][CH2:16][CH2:15][N:12]1[CH:9]2[CH2:10][CH2:11][CH:1]1[C:2]1[CH:3]=[C:4]([NH2:13])[CH:5]=[CH:6][C:7]=1[CH2:8]2

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 809722-Bromoethyl methyl etherHCID 6726400912-Aza-tricyclo[7.2.1.0*2,7*]dodeca-2(7),3,5-trien-4-ylamine

Product 1

HCID 6726400112-(2-Methoxy-ethyl)-12-aza-tricyclo[7.2.1.0(2,7)]dodeca-2(7),3,5-trien-4-ylamineYield 13%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

12-Aza-tricyclo[7.2.1.0*2,7*]dodeca-2(7),3,5-trien-4-ylamine (J. Med. Chem. 1988, 31, 433-444) (150 mg, 0.86 mmol), 1-bromo-2-methoxy-ethane (120 mg, 0.86 mmol) and potassium carbonate (119 mg, 0.86 mmol) were stirred together in acetone (5 mL) at 50° C. for 6 h. The mixture was filtered and concentrated before purifying on silica gel chromatography (0-50% MeOH in CH2Cl2) to obtain 12-(2-Methoxy-ethyl)-12-aza-tricyclo[7.2.1.0*2,7*]dodeca-2(7),3,5-trien-4-ylamine as a clear oil (25 mg, 13%). MS (m/e) 233 (M+1).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated
  3. custombefore purifying on silica gel chromatography (0-50% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-2188f05509bc42ec946a1b470c35c712
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

Loading…