Potassium Carbonate → HCID 70564249, compound

HRID 126915Notes

Reaction equation

HRID 126915 reaction equation
[CH:1]1([N:7]2[CH2:11][C@@H:10]([NH:12][CH3:13])[C@H:9]([OH:14])[CH2:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].[C:21]1([C:31]([Cl:33])=[O:32])[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:24]=[CH:23][CH:22]=1>C(Cl)Cl>[ClH:33].[CH:1]1([N:7]2[CH2:8][C@@H:9]([OH:14])[C@H:10]([N:12]([CH3:13])[C:31]([C:21]3[C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[CH:24]=[CH:23][CH:22]=3)=[O:32])[CH2:11]2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 701461-Naphthalenecarbonyl chlorideHCID 70563700HCID 70563700, compound

Product 1

HCID 70564249HCID 70564249, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 10 g (0.05 mole) of trans-1-cyclohexyl-4-methylamino-3-pyrrolidinol in 100 ml of methylene chloride was mixed with 10 g of powdered anhydrous potassium carbonate and stirred while a solution of 10 g (0.05 mole) of 1-naphthoyl chloride in 50 ml of methylene chloride was added dropwise. The mixture was stirred for 2 hrs and then heated at reflux for 24 hrs. After cooling, the mixture was washed with water and the organic fraction was evaporated under vacuum. The residue was chromatographed on silica gel, eluting with acetone. Ten grams of the base, 56% yield, were collected and converted to the hydrochloride. After recrystallization from isopropyl alcohol, the salt melted at 238°-241° C.

Workup

  1. additionwas added dropwise
  2. temperatureheated
  3. temperatureat reflux for 24 hrs
  4. temperatureAfter cooling
  5. washthe mixture was washed with water
  6. customthe organic fraction was evaporated under vacuum
  7. customThe residue was chromatographed on silica gel
  8. washeluting with acetone
  9. customTen grams of the base, 56% yield, were collected
  10. customAfter recrystallization from isopropyl alcohol

Sources & evidence

ORD record
ord-5519663de7444ef08096d6ea71d50b42
Source dataset
uspto-grants-1981_03
Patent number
US04254135

Reaction notes

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