Potassium Carbonate → HCID 67065317, compound

HRID 535798Notes

Reaction equation

HRID 535798 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.[Cl:8][CH2:9][CH2:10][NH:11][C@@H:12]1[CH2:14][C@H:13]1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[ClH:8].[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:9][CH2:10][NH:11][C@@H:12]2[CH2:14][C@H:13]2[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 531671-MethylpiperazineHCID 67064917HCID 67064917, compound2×

Product 1

HCID 67065317HCID 67065317, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

N-methyl piperazine, 0.68 mL (6.13 mmol), was added over a solution of the N-(2-chloroethyl)-N-[(trans)-2-phenylcyclopropyl]amine (Intermediate B) 0.6 g (3.06 mmol) in 60 mL DMF, followed by the addition of K2CO3 (3.06 mmol). The mixture was stirred at 80° C. and the progression was monitored by TLC, after completion, the solvent was evaporated to dryness. DCM and a K2CO3 solution were added to the crude. The organic layer was extracted, washed with water, brine and dried with MgSO4 and filtered. The crude was purified by silica gel chromatography (DCM-MeOH from 100:0 to 80:20). HCl (2M in diethyl ether), 3 mL, was added dropwise to a solution of the N-[(trans)-2-phenylcyclopropyl]ethane-1,2-diamine derivative in diethyl ether (10 mL) until solid precipitation. The mixture was stirred for 2 hours, the solid was filtered, washed with diethyl ether and dried under reduced pressure to give 0.58 g of N-[2-(4-methylpiperazin-1-yl)ethyl]-N-[(trans)-2-phenylcyclopropyl]amine hydrochloride salt. Yield: 56%. 1HNMR (DMSO-d6) δ (ppm): 1.24 (q, 1H), 1.63 (quin, 1H), 2.62 (m, 1H), 2.78 (s, 3H), 3.00 (m, 1H), 3.28 (br, 4H), 3.73 (br, 2H), 3.44 (br, 2H), 3.61 (br, 4H), 7.17 (t, 2H), 7.20 (d, 1H), 7.28 (t, 2H), 10.12 (br, 1H), 11.90 (br, 1H). MS (M+H): 260.09

Workup

  1. customafter completion, the solvent was evaporated to dryness
  2. additionDCM and a K2CO3 solution were added to the crude
  3. extractionThe organic layer was extracted
  4. washwashed with water, brine
  5. dry with materialdried with MgSO4
  6. filtrationfiltered
  7. customThe crude was purified by silica gel chromatography (DCM-MeOH from 100:0 to 80:20)
  8. additionHCl (2M in diethyl ether), 3 mL, was added dropwise to a solution of the N-[(trans)-2-phenylcyclopropyl]ethane-1,2-diamine derivative in diethyl ether (10 mL) until solid precipitation
  9. stirringThe mixture was stirred for 2 hours
  10. filtrationthe solid was filtered
  11. washwashed with diethyl ether
  12. customdried under reduced pressure

Sources & evidence

ORD record
ord-d152e86a80124f0ca9394529ed917988
Source dataset
uspto-grants-2014_10
Patent number
US08859555B2

Reaction notes

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