HCID 2723642, compound → HCID 178508967, compound

HRID 16428Notes

Reaction equation

HRID 16428 reaction equation
[N:1]1([C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:11])[CH2:6][CH2:5][CH2:4][CH:3]([C:7]([O-])=O)[CH2:2]1.Cl.[CH3:21]N(C)CCCN=C=NCC.[C:32](=[O:35])([O-])[O-].[NH2:36][C:37]([NH2:39])=[NH2+:38].NC(N)=[NH2+]>CN(C)C1C=CN=CC=1.ClCCl>[NH2:38][C:37]1[N:39]=[C:7]([CH:3]2[CH2:4][CH2:5][CH2:6][N:1]([C:10]([O:12][CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[O:11])[CH2:2]2)[CH:21]=[C:32]([OH:35])[N:36]=1

Participants

6

Reactant 3

HCID 2723642HCID 2723642, compoundHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 21436258HCID 21436258, compound

Product 1

HCID 178508967HCID 178508967, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

2 g (7.59 mmol) of 1-benzyl piperidine-1,3-dicarboxylate, 1.31 g (9.11 mmol) of 2,2-dimethyl-1,3-dioxolane-4,6-dione and 1.85 g (15.19 mmol) of 4-dimethylamino-pyridine are initially charged in 12 ml of dichloromethane, and the mixture is cooled to 0° C. 1.60 g (8.35 mmol) of (3-dimethylaminopropyl)ethylcarbodiimide hydrochloride are added. The mixture is stirred at 0° C. for one hour and then at room temperature for 18 hours. The reaction mixture is diluted with dichloromethane (50 ml) and washed successively with water (20 ml), 1N hydrochloric acid (30 ml), saturated aqueous sodium bicarbonate solution (30 ml) and saturated aqueous sodium chloride solution. The organic phase is dried over anhydrous magnesium sulfate. The solution is concentrated under reduced pressure. The residue (1.2 g) is dissolved in 30 ml of ethanol, 0.13 ml (0.61 mmol) of 37% strength hydrochloric acid is added and the mixture is stirred under reflux for one hour. After cooling, 0.59 g (3.18 mmol) of guanidinium carbonate is added and the reaction mixture is stirred at reflux (oil bath temperature 93° C.) for 18 hours. The solution is concentrated. The crude product is purified on a silica gel column using dichloromethane/methanol 20:1. This gives 0.68 g (27% of theory) of product.

Workup

  1. waitat room temperature for 18 hours
  2. washwashed successively with water (20 ml), 1N hydrochloric acid (30 ml), saturated aqueous sodium bicarbonate solution (30 ml) and saturated aqueous sodium chloride solution
  3. dry with materialThe organic phase is dried over anhydrous magnesium sulfate
  4. concentrationThe solution is concentrated under reduced pressure
  5. dissolutionThe residue (1.2 g) is dissolved in 30 ml of ethanol
  6. addition0.13 ml (0.61 mmol) of 37% strength hydrochloric acid is added
  7. stirringthe mixture is stirred
  8. temperatureunder reflux for one hour
  9. temperatureAfter cooling
  10. stirringthe reaction mixture is stirred
  11. temperatureat reflux (oil bath temperature 93° C.) for 18 hours
  12. concentrationThe solution is concentrated
  13. customThe crude product is purified on a silica gel column

Sources & evidence

ORD record
ord-1f4ac67eaa5e407299b8a6a12365f71f
Source dataset
uspto-grants-2010_06
Patent number
US07737153B2

Reaction notes

Loading…