Acridan → 10-[1-(2-Pyrrolin-2YL)-2-pyrrolin-2-YL]acridan

HRID 267918Notes

Reaction equation

HRID 267918 reaction equation
[CH:1]1[C:14]2[CH2:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[NH:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.Cl.Cl[C:17]1[N:18]([C:22]2[CH2:26][CH2:25][CH2:24][N:23]=2)[CH2:19][CH2:20][CH:21]=1>ClCCCl>[NH:23]1[CH2:24][CH2:25][CH:26]=[C:22]1[N:18]1[CH2:19][CH2:20][CH:21]=[C:17]1[N:6]1[C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH2:13][C:14]2[CH:1]=[CH:2][CH:3]=[CH:4][C:5]1=2

Participants

4

Reactant 2

HCID 7106AcridanHCID 203071382-Chloro-1-(1-pyrrolin-2-yl) 2-pyrroline hydrochloride

Product 1

HCID 7061762010-[1-(2-Pyrrolin-2YL)-2-pyrrolin-2-YL]acridan

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A mixture of acridan (3.6 g., 0.02 mole) and 2-chloro-1-(1-pyrrolin-2-yl) 2-pyrroline hydrochloride (5.1 g., 0.025 mole), obtained according to the method of H. Brederick, et al., Chem. Ber., 94, 2292 (1961), in 50 ml. of 1,2-dichloroethane is refluxed for a period of 15 hr. The mixture is sequentially extracted with 50 ml. of 1.5N hydrochloric acid and three 50 ml. portions of water. The combined acid-water extracts are basified with 5N potassium hydroxide, extracted with ether and the ethereal extract concentrated. Crystallization of the residue thus obtained from ethanol affords the free base 10-[1-(2-PYRROLIN-2YL)-2-PYRROLIN-2-YL]ACRIDAN, m.p. 179°-181° C. which is converted according to the procedure of Example 1 to 10-[1-(2-PYRROLIN-2-YL)-2-PYRROLIN-2-YL]ACIDAN HYDROCHLORIDE, m.p. 212.5°-216.5° C. (dec.) (corr.)., from ethanol-ether.

Workup

  1. customobtained
  2. extractionThe mixture is sequentially extracted with 50 ml
  3. extractionextracted with ether
  4. extractionthe ethereal extract
  5. concentrationconcentrated
  6. customCrystallization of the residue
  7. customthus obtained from ethanol

Sources & evidence

ORD record
ord-690243ae09a343ef98ba51e5f75135d6
Source dataset
uspto-grants-1976_03
Patent number
US03946004

Reaction notes

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