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

HRID 2309728Notes

Reaction equation

Cl[CH2:2][CH2:3][O:4][C:5]1[CH:6]=[CH:7][C:8]2[C:17]([CH:18]=1)=[N:16][C:15]1[C:10](=[CH:11][CH:12]=[C:13]([O:19][CH2:20][CH2:21]Cl)[CH:14]=1)[CH:9]=2.[NH:23]1[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1>>[N:23]1([CH2:2][CH2:3][O:4][C:5]2[CH:6]=[CH:7][C:8]3[C:17]([CH:18]=2)=[N:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([O:19][CH2:20][CH2:21][N:16]4[CH2:17][CH2:8][CH2:9][CH2:10][CH2:15]4)[CH:14]=2)[CH:9]=3)[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1

Participants

Reactant 2

HCID 8082Piperidine

HCID 201846663,6-Bis(2-chloroethoxy)acridine

Product 1

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

Procedure

In accordance with the above flowchart, a 3,6-bis(2-chloroethoxy)acridine (1), where R1 is as described hereinabove, is reacted with piperidine in a steel bomb at about 60° to about 1000° C. for about 18 to about 36 hours, giving a 3,6-bis(2-piperidinoethoxy)acridine (3) which is then dissolved in methanol, treated with excess 30% hydrogen peroxide for about 12 to about 48 hours, then with platinum catalyst to destroy the excess peroxide and is purified by dry column chromatography on silica gel using the developing system methanol:triethylamine (20:1, v/v). The length of reaction time with hydrogen peroxide is the determining factor in whether a mono-oxide (4) or dioxide (5) is produced.

Sources & evidence

ORD record: ord-23f96c3fcdf741189732d76f55b2f23e
Source dataset: uspto-grants-1987_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04696936

Reaction notes

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