1,4-Bis(3-aminopropyl)piperazine → HCID 54371305, compound

HRID 1952883Notes

Reaction equation

HRID 1952883 reaction equation
[N-]1[CH:5]=[CH:4][N:3]=[CH:2]1.[CH:6]1[C:19]2[C:10](=[N:11][C:12]3[C:17]([CH:18]=2)=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:9]([C:20]([OH:22])=O)=[CH:8][CH:7]=1.[NH2:23][CH2:24][CH2:25][CH2:26][N:27]1[CH2:32][CH2:31][N:30]([CH2:33][CH2:34][CH2:35][NH2:36])[CH2:29][CH2:28]1>>[CH:6]1[C:19]2[C:10](=[N:11][C:12]3[C:17]([CH:18]=2)=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:9]([C:20]([NH:36][CH2:35][CH2:34][CH2:33][N:30]2[CH2:29][CH2:28][N:27]([CH2:26][CH2:25][CH2:24][NH:23][C:20]([C:9]3[C:4]4[C:5](=[CH:16][C:17]5[C:2]([N:3]=4)=[CH:15][CH:14]=[CH:13][CH:12]=5)[CH:6]=[CH:7][CH:8]=3)=[O:22])[CH2:32][CH2:31]2)=[O:22])=[CH:8][CH:7]=1

Participants

3

Reactant 2

HCID 816291,4-Bis(3-aminopropyl)piperazineHCID 86755727HCID 86755727, compound

Product 1

HCID 54371305HCID 54371305, compoundYield 91%

Procedure

Similar reaction of acridine-4-carboxylic acid imidazolide with 1,4-bis(3-aminopropyl)piperazine as above, and crystallization of the crude product from CH2Cl2 /EtOAc/iPr2O, gave N1,N4-bis[(acridine-4-carboxamido)propyl]piperazine (36) (91%). 1H NMR [(CD3)2SO] δ 11.39 (t, J=5.2 Hz, 2 H, 2×CONH), 9.33 (s, 2 H, H-9), 8.73 (d, J=7.0 Hz, 2 H, H-3), 8.38 (d, J=8.5 Hz, 2 H, ArH), 8.32-8.20 (m, 4 H, ArH), 7.97 (t, J=7.8 Hz, 2 H, ArH), 7.82-7.63 (m, 4 H, ArH), 3.57 (q, J=6.0 Hz, 4 H, 2×NHCH2), 2.6-2.3 t (m, 12 H, H-piperazine, 2×CH2CH2CH2N), 1.85 (quint, J=6.7 Hz, 4 H, CH2CH2CH2). Crystallization from MeOH/EtOAc/HCl gave the tetrahydrochloride salt, mp 248-253° C. Anal. (C38H38N6O2.4HCl) C, H, N, Cl.

Workup

  1. customcrystallization of the crude product from CH2Cl2 /EtOAc/iPr2O

Sources & evidence

ORD record
ord-565067bf7a614be3aebeff89daf20ee1
Source dataset
uspto-grants-2000_09
Patent number
US06114332

Reaction notes

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