4-Nitrobenzoyl chloride → HCID 70564549, compound

HRID 126911Notes

Reaction equation

HRID 126911 reaction equation
[NH2:1][CH:2]1[CH2:6][N:5]([CH:7]2[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]2)[CH2:4][CH:3]1[OH:13].C(=O)([O-])[O-].[K+].[K+].[N+:20]([C:23]1[CH:31]=[CH:30][C:26]([C:27](Cl)=[O:28])=[CH:25][CH:24]=1)([O-:22])=[O:21]>C(Cl)Cl>[CH:7]1([N:5]2[CH2:4][C@@H:3]([OH:13])[C@H:2]([NH:1][C:27](=[O:28])[C:26]3[CH:25]=[CH:24][C:23]([N+:20]([O-:22])=[O:21])=[CH:31][CH:30]=3)[CH2:6]2)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1

Participants

5

Reactant 3

HCID 85024-Nitrobenzoyl chlorideHCID 11430Potassium CarbonateHCID 10154346HCID 10154346, compound

Product 1

HCID 70564549HCID 70564549, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 1.84 g (0.01 mole) of 4-amino-1-cyclohexyl-3-pyrrolidinol in 50 ml of methylene chloride was cooled to 5° C. and 2 g of powdered, anhydrous potassium carbonate was added. The mixture was stirred while a solution of 1.86 g of p-nitrobenzoyl chloride in 20 ml of methylene chloride was added dropwise. The mixture was then allowed to warm to room temperature and was stirred for one hour. The slurry was filtered, and the residue, after solvent evaporation, crystallized immediately and was recrystallized from acetone. Yield was 3.0 g (90%), m.p. 155.5°-157.0° C.

Workup

  1. additionwas added dropwise
  2. filtrationThe slurry was filtered
  3. customthe residue, after solvent evaporation
  4. customcrystallized immediately
  5. customwas recrystallized from acetone

Sources & evidence

ORD record
ord-15991e0d787e452084122046bedac02d
Source dataset
uspto-grants-1981_03
Patent number
US04254135

Reaction notes

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