Pyrrolidine → HCID 135783945, compound

HRID 1578522Notes

Reaction equation

HRID 1578522 reaction equation
Cl[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:19]=[CH:18][CH:17]=[C:16]2[C:7]=1[N+:8]([O-:22])=[C:9]1[C:14](=[N+:15]2[O-:20])[C:13]([OH:21])=[CH:12][CH:11]=[CH:10]1.[NH:23]1[CH2:27][CH2:26][CH2:25][CH2:24]1>C(Cl)(Cl)Cl>[N:23]1([CH2:2][CH2:3][CH2:4][O:5][C:6]2[CH:19]=[CH:18][CH:17]=[C:16]3[C:7]=2[N+:8]([O-:22])=[C:9]2[C:14](=[N+:15]3[O-:20])[C:13]([OH:21])=[CH:12][CH:11]=[CH:10]2)[CH2:27][CH2:26][CH2:25][CH2:24]1

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 135783957HCID 135783957, compound

Product 1

HCID 135783945HCID 135783945, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

2.0 grams of 6-(3-chloropropoxy)-1-phenazinol 5,10-dioxide and 20ml of pyrrolidine were placed in a flask and stirred at room temperature for 3 1/2 hours. The reaction mixture was diluted with CHCl3 and washed repeatedly with water until the water washes were neutral. The chloroform solution was extracted with 3 × 150 ml of 10 percent aqueous HCl. The acid extracts were combined, neutralized with sodium carbonate, extracted with CHCl3 and the combined CHCl3 extracts were washed with water and dried over sodium sulfate and concentrated in vacuo. The residue was recrystallized from acetone. The solids were filtered and washed with a little ether and dried in vacuo at 50° for 16 hours to yield metallic red crystals of 6-(3-pyrrolidinopropoxy)-1-phenazinol 5,10-dioxide, m.p. 113°-114°C (dec.).

Workup

  1. washwashed repeatedly with water until the water washes
  2. extractionThe chloroform solution was extracted with 3 × 150 ml of 10 percent aqueous HCl
  3. extractionextracted with CHCl3
  4. washthe combined CHCl3 extracts were washed with water
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was recrystallized from acetone
  8. filtrationThe solids were filtered
  9. washwashed with a little ether
  10. customdried in vacuo at 50° for 16 hours

Sources & evidence

ORD record
ord-3d8c2ef7b9d44c109991d1f0a793e1b1
Source dataset
uspto-grants-1976_02
Patent number
US03937707

Reaction notes

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