Bis(3-aminopropyl)amine → HCID 23299929, compound

HRID 1952882Notes

Reaction equation

HRID 1952882 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][NH:27][CH2:28][CH2:29][CH2:30][NH2:31]>>[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:23][CH2:24][CH2:25][CH2:26][NH:27][CH2:28][CH2:29][CH2:30][NH:31][C:20]([C:9]2[C:2]3[C:19](=[CH:18][C:5]4[C:4]([N:3]=3)=[CH:17][CH:12]=[CH:13][CH:14]=4)[CH:6]=[CH:7][CH:8]=2)=[O:22])=[O:22])=[CH:8][CH:7]=1

Participants

3

Reactant 2

HCID 5942Bis(3-aminopropyl)amineHCID 86755727HCID 86755727, compound

Product 1

HCID 23299929HCID 23299929, compoundYield 80%

Procedure

Similar reaction of acridine-4-carboxylic acid imidazolide with N,N-bis(3-aminopropyl)amine as above, followed by purification of the product by chromatography on alumina-90, eluting with CH2Cl2 /MeOH (20:1), gave bis[3-(acridine-4-carboxamido)propyl]amine (35) (80%) as an oil. 1H NMR [(CD3)2SO] δ 11.40 (t, J=5.4 Hz, 2 H, 2×CONH), 9.19 (s, 2 H, H-9), 8.71 (d, J=7.1 Hz, 2 H, H-3), 8.32 (d, J=8.5 Hz, 2 H, ArH), 8.18-8.00 (m, 4 H, ArH), 7.83-7.62 (m, 4 H, ArH), 7.51 (t, J=7.5 Hz, 2H, ArH), 3.64 (q, J=6.0 Hz, 4H, 2×CONHCH2) 2.86 (t, J=6.7 Hz, 4H, CH2NHCH2) 1.92 (quint, J=6.5 Hz, 4 H, 2×CH2CH2CH2). Crystallization from MeOH/EtOAc/HCl gave the trihydrochloride salt, mp 171-173° C. Anal. (C34H31N5O2.2HCl.2H2O) C, H, N, Cl.

Workup

  1. customfollowed by purification of the product by chromatography on alumina-90
  2. washeluting with CH2Cl2 /MeOH (20:1)

Sources & evidence

ORD record
ord-93a8498e5bb643bd8955f35b45abfa41
Source dataset
uspto-grants-2000_09
Patent number
US06114332

Reaction notes

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