Piperidine → Acridine, 3,6-bis(2-(1-piperidinyl)ethoxy)-

HRID 979104Notes

Reaction equation

HRID 979104 reaction equation
Cl.Cl[CH2:3][CH2:4][O:5][C:6]1[CH:7]=[CH:8][C:9]2[C:18]([CH:19]=1)=[N:17][C:16]1[C:11](=[CH:12][CH:13]=[C:14]([O:20][CH2:21][CH2:22]Cl)[CH:15]=1)[CH:10]=2.[NH:24]1[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1>>[N:24]1([CH2:3][CH2:4][O:5][C:6]2[CH:7]=[CH:8][C:9]3[C:18]([CH:19]=2)=[N:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:20][CH2:21][CH2:22][N:17]4[CH2:18][CH2:9][CH2:10][CH2:11][CH2:16]4)[CH:15]=2)[CH:10]=3)[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1

Participants

3

Reactant 2

HCID 8082PiperidineHCID 201846653,6-Bis(2-chloroethoxy)acridine--hydrogen chloride (1/1)

Product 1

HCID 133712Acridine, 3,6-bis(2-(1-piperidinyl)ethoxy)-

Procedure

A suspension of 3,6-bis(2-chloroethoxy)acridine hydrochloride in piperidine was heated in a steel bomb at 80° C. for 24 hours. The excess piperidine was removed in vacuo and the residual solution was washed twice with 30 ml portions of saturated aqueous sodium bicarbonate and filtered. The filtrate was evaporated to a residue, giving 3,6-bis(2-piperidinoethoxy)acridine as yellow crystals, mp 129°-130° C.

Workup

  1. customThe excess piperidine was removed in vacuo
  2. washthe residual solution was washed twice with 30 ml portions of saturated aqueous sodium bicarbonate
  3. filtrationfiltered
  4. customThe filtrate was evaporated to a residue

Sources & evidence

ORD record
ord-672f57c7110b442d935da12e8fcfa842
Source dataset
uspto-grants-1987_05
Patent number
US04666917

Reaction notes

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