2-Bromopropane → HCID 13054428, compound

HRID 620244Notes

Reaction equation

HRID 620244 reaction equation
[CH3:1][NH:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C(=O)([O-])[O-].[K+].[K+].[CH:16](Br)([CH3:18])[CH3:17]>CC(C)CC(=O)C>[CH:16]([N:2]([CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH3:1])([CH3:18])[CH3:17]

Participants

5

Reactant 3

HCID 63582-BromopropaneHCID 7669N-MethylbenzylamineHCID 11430Potassium Carbonate

Product 1

HCID 13054428HCID 13054428, compound

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

A flask containing N-methylbenzylamine (3.87 ml, 3.63 g, 0.03 moles), potassium carbonate (8.29 g, 0.06 moles) and 4-methyl-2-pentanone (100 ml) was treated with isopropyl bromide (2.69 ml, 0.03 moles) then heated under reflux for 18 hours. The reaction was checked by thin layer chromatography (tlc) to ensure the starting materials had been consumed. The reaction mixture was gravity filtered hot to remove the potassium salts and the filtrate was concentrated to an oil under reduced pressure on the rotovap. The oil was purified by flash chromatography (davisil 633, 20% ethyl acetate/hexane). The appropriate fractions were pooled and concentrated to an oil which was dissolved in anhydrous diethyl ether. The ether solution was treated with gaseous HCl. The ether was removed under reduced pressure. The residue was dissolved in absolute ethanol, treated with activated carbon, filtered, and cooled. The liquid was concentrated with acetone to remove traces of water. The solid was collected by vacuum filtration. m.p. 127.5°-128.5° C. Proton NMR (CDC13 +TMS) 1.36 doublet J= 6.66 Hz 3 H ipr methyl, 1.51 doublet J=6.66 Hz 3 H ipr methyl, 1.88 ppm NH+, 2.62 doublet J=5.04 Hz 3 H N-Methyl, 3.47 septette 1 H tertiary, 4.15 doublet J=6.05 Hz 2 H benzylic CH2 --, 7.28-7.42 5 H aromatic; C-13 (DMSO) ref:39.5, 131.16(11.88), 130.53(8.72), 129.12(5.74), 128.56 (10.92), 55.99(2.06), 55.11(7.14), 39.51(1.48), 34.36(6.93), 1845(3.11), 16.89(6.18), 15 19(5.20). EI Mass spec. M/e-(int) M+163(6.3), 148(40.7), 120(1.2), 92(8.0), 91(100), 90(1.5), 89(3.1), 78(2.2), 77(4.1), 65(18.8), 57(1.6), 56(8.1), 51(3.5), 44(6.0), 43(3.5) 42(11.8), 41(5.2).

Workup

  1. temperaturethen heated
  2. temperatureunder reflux for 18 hours
  3. customhad been consumed
  4. filtrationfiltered hot
  5. customto remove the potassium salts
  6. concentrationthe filtrate was concentrated to an oil under reduced pressure on the rotovap
  7. customThe oil was purified by flash chromatography (davisil 633, 20% ethyl acetate/hexane)
  8. concentrationconcentrated to an oil which
  9. dissolutionwas dissolved in anhydrous diethyl ether
  10. additionThe ether solution was treated with gaseous HCl
  11. customThe ether was removed under reduced pressure
  12. dissolutionThe residue was dissolved in absolute ethanol
  13. additiontreated with activated carbon
  14. filtrationfiltered
  15. temperaturecooled
  16. concentrationThe liquid was concentrated with acetone
  17. customto remove traces of water
  18. filtrationThe solid was collected by vacuum filtration

Sources & evidence

ORD record
ord-b6ccb65e0f864e0dbc13762b42806af5
Source dataset
uspto-grants-1989_04
Patent number
US04820737

Reaction notes

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