Sodium Iodide → HCID 178453978, compound

HRID 722023Notes

Reaction equation

HRID 722023 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:14][CH2:13][C@H:12]([NH2:15])[CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl[CH2:17][CH2:18][CH2:19][CH2:20]Cl.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>O.C(O)C.O>[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:10][CH2:11][C@H:12]([N:15]2[CH2:20][CH2:19][CH2:18][CH2:17]2)[CH2:13][CH2:14]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 80591,4-DichlorobutaneHCID 11430Potassium CarbonateHCID 178419079HCID 178419079, compound

Product 1

HCID 178453978HCID 178453978, compoundYield 72.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 19096565Water ethanolSolvent

Conditions

Temperature
90 °C

Procedure

A mixture comprising 500 mg of N-tert-butoxycarbonyl-trans-1,4-cyclohexanediamine, 326 mg of 1,4-dichlorobutane, 805 mg of potassium carbonate, 70 mg of sodium iodide and ethanol-water (8 ml–2 ml) was stirred at 90° C. for 12 days. Water was added to the reaction mixture, and the resulting mixture was extracted with chloroform. The extract was washed with brine, dried over anhydrous sodium sulfate, and then, the solvent was removed under reduced pressure. The obtained residue was purified by silica gel flash column chromatography (solvent: chloroform-methanol-aqueous ammonia=100/5/0.5 to 100/10/0.5) to obtain 453 mg of N-tert-butoxycarbonyl trans-4-(1-pyrrolidinyl)cyclohexylamine.

Workup

  1. extractionthe resulting mixture was extracted with chloroform
  2. washThe extract was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe solvent was removed under reduced pressure
  5. customThe obtained residue was purified by silica gel flash column chromatography (solvent: chloroform-methanol-aqueous ammonia=100/5/0.5 to 100/10/0.5)

Sources & evidence

ORD record
ord-6e1d55103dd3434d90fa6c589d162a82
Source dataset
uspto-grants-2006_11
Patent number
US07138397B2

Reaction notes

Loading…