Chloroform → HCID 22761198, compound

HRID 1658374Notes

Reaction equation

HRID 1658374 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8](Cl)=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].C(Cl)(Cl)Cl.[C:17]1([N:23]2[CH2:27][CH2:26][CH:25]([NH2:28])[CH2:24]2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(=O)([O-])[O-].[K+].[K+]>O>[C:17]1([N:23]2[CH2:27][CH2:26][CH:25]([NH:28][C:8](=[O:9])[C:7]3[CH:11]=[CH:12][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=3)[CH2:24]2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 6212Chloroform2×HCID 85024-Nitrobenzoyl chlorideHCID 11430Potassium CarbonateHCID 114009521-phenylpyrrolidin-3-amine

Product 1

HCID 22761198HCID 22761198, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 6.9 g. (0.037 mole) of p-nitrobenzoyl chloride in 30 ml. of chloroform was added dropwise at room temperature to a stirred mixture of 6 g. (0.037 mole) of 1-phenyl-3-aminopyrrolidine in 30 ml. of chloroform and 10 g. of potassium carbonate in 30 ml. of water. After addition, the mixture was stirred an additional 30 minutes. The chloroform layer was separated, dried over magnesium sulfate and evaporated to a solid. Recrystallization of the crude product from ethanol-water solution gave 10.6 g. (92%) of orange solid which melted at 153°-155°C.

Workup

  1. additionAfter addition
  2. customThe chloroform layer was separated
  3. dry with materialdried over magnesium sulfate
  4. customevaporated to a solid
  5. customRecrystallization of the crude product from ethanol-water solution
  6. customgave 10.6 g

Sources & evidence

ORD record
ord-ed552eda786d4e3692c6d529180107e8
Source dataset
uspto-grants-1976_06
Patent number
US03963745

Reaction notes

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