Hydrochloric Acid → Iptakalim Hydrochloride

HRID 227287Notes

Reaction equation

HRID 227287 reaction equation
[CH3:1][CH:2]([NH:4][C:5]([CH3:10])([CH:7]([CH3:9])[CH3:8])[CH3:6])[CH3:3].[ClH:11]>C(O)C>[CH3:1][CH:2]([NH:4][C:5]([CH3:10])([CH:7]([CH3:9])[CH3:8])[CH3:6])[CH3:3].[ClH:11]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 10057607642407-44-1

Product 1

HCID 11446679Iptakalim HydrochlorideYield 95.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 100.0 g N-(1-methylethyl)-2,3-dimethyl-2-butylamine in 200 mL ethanol, 100 mL hydrochloric acid was added with shaking and cooling in an glacial water bath. The solvent was distilled off to dry in vacuum. The residue was dissolve in ethanol, then distilled off to dry in vacuum and crystallized from 1:1 i-PrOH-c-Hex-H to give a solid 130.5 g (95.5%), mp 228-230° C.(i-PrOH:Et2O). Elemental analysis for C9H22ClN(%): Calculated C, 60.14; H, 12.34; N, 7.79; Cl, 19.73. Found C, 60.14; H, 12.48; N, 7.31; Cl, 19.67. 1H-NMR (D2O, ppm) 0.98(d, J=6.75H, 6H), 1.33(s, 6H), 1.37(d, J=6.46, 6H), 2.10(m, 1H), 3.70(m, 1H). MS(m/z) 143(M+), 100(B).

Workup

  1. temperaturecooling in an glacial water bath
  2. distillationThe solvent was distilled off
  3. customto dry in vacuum
  4. dissolutionThe residue was dissolve in ethanol
  5. distillationdistilled off
  6. customto dry in vacuum
  7. customcrystallized from 1:1 i-PrOH-c-Hex-H

Sources & evidence

ORD record
ord-933aad5b0f9948f084f4bb379f37a72c
Source dataset
uspto-grants-2009_07
Patent number
US07560473B2

Reaction notes

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