Benzoyl chloride → HCID 70565138, compound

HRID 126912Notes

Reaction equation

HRID 126912 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]([Cl:29])(=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C(Cl)Cl>[ClH:29].[CH:1]1([N:7]2[CH2:8][C@@H:9]([OH:14])[C@H:10]([N:12]([CH3:13])[C:21](=[O:28])[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH2:11]2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 11430Potassium CarbonateHCID 70563700HCID 70563700, compound

Product 1

HCID 70565138HCID 70565138, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of trans-1-cyclohexyl-4-methylamino-3-pyrrolidinol (19.8 g) in 200 ml of methylene chloride was cooled to 5° C. and 20 g of powdered, anhydrous potassium carbonate was added. The mixture was stirred and cooled while 14.1 g of benzoyl chloride in 100 ml of methylene chloride was added dropwise. The mixture was allowed to come to room temperature and stirred for 24 hr., then heated at reflux for 5 hrs. The mixture was cooled and extracted with water. The methylene chloride was evaporated and the residue was converted to the hydrochloride and recrystallized twice from isopropyl alcohol, m.p. 184°-186.5° C.

Workup

  1. additionwas added dropwise
  2. customto come to room temperature
  3. stirringstirred for 24 hr
  4. temperature, then heated
  5. temperatureat reflux for 5 hrs
  6. temperatureThe mixture was cooled
  7. extractionextracted with water
  8. customThe methylene chloride was evaporated
  9. customrecrystallized twice from isopropyl alcohol, m.p. 184°-186.5° C.

Sources & evidence

ORD record
ord-fb2f1070017d4c25a35cd40296f20725
Source dataset
uspto-grants-1981_03
Patent number
US04254135

Reaction notes

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