1,8-Octanediamine, 4-(aminomethyl)- → 1,8-Bis[N-(2,4-bis[N-octyl-N-(2,2,6,6-tetramethylpiperid-4-yl)amino]-1,3,5-triazin-6-yl)amino]-4-[N-(2,4-bis[N-octyl-N-(2,2,6,6-tetramethylpiperid-4-yl)amino]-1,3,5-triazin-6-yl)aminomethyl]octane

HRID 484945Notes

Reaction equation

HRID 484945 reaction equation
Cl[C:2]1[N:7]=[C:6]([N:8]([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH:9]2[CH2:14][C:13]([CH3:16])([CH3:15])[NH:12][C:11]([CH3:18])([CH3:17])[CH2:10]2)[N:5]=[C:4]([N:27]([CH:36]2[CH2:41][C:40]([CH3:43])([CH3:42])[NH:39][C:38]([CH3:45])([CH3:44])[CH2:37]2)[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[N:3]=1.[NH2:46][CH2:47][CH2:48][CH2:49][CH:50]([CH2:56][NH2:57])[CH2:51][CH2:52][CH2:53][CH2:54][NH2:55]>C1(C)C(C)=CC=CC=1>[CH2:28]([N:27]([C:4]1[N:5]=[C:6]([N:8]([CH:9]2[CH2:10][C:11]([CH3:17])([CH3:18])[NH:12][C:13]([CH3:15])([CH3:16])[CH2:14]2)[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[N:7]=[C:2]([NH:46][CH2:47][CH2:48][CH2:49][CH:50]([CH2:56][NH:57][C:2]2[N:3]=[C:4]([N:27]([CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[CH:36]3[CH2:37][C:38]([CH3:44])([CH3:45])[NH:39][C:40]([CH3:43])([CH3:42])[CH2:41]3)[N:5]=[C:6]([N:8]([CH:9]3[CH2:10][C:11]([CH3:18])([CH3:17])[NH:12][C:13]([CH3:15])([CH3:16])[CH2:14]3)[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[N:7]=2)[CH2:51][CH2:52][CH2:53][CH2:54][NH:55][C:2]2[N:3]=[C:4]([N:27]([CH:36]3[CH2:37][C:38]([CH3:44])([CH3:45])[NH:39][C:40]([CH3:43])([CH3:42])[CH2:41]3)[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[N:5]=[C:6]([N:8]([CH:9]3[CH2:10][C:11]([CH3:18])([CH3:17])[NH:12][C:13]([CH3:15])([CH3:16])[CH2:14]3)[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[N:7]=2)[N:3]=1)[CH:36]1[CH2:37][C:38]([CH3:45])([CH3:44])[NH:39][C:40]([CH3:42])([CH3:43])[CH2:41]1)[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35]

Participants

4

Reactant 2

HCID 942111,8-Octanediamine, 4-(aminomethyl)-HCID 202721352-chloro-4,6-bis[N-octyl-N-(2,2,6,6-tetramethyl-4-piperidyl)amino]-1,3,5-triazine

Product 1

HCID 202721301,8-Bis[N-(2,4-bis[N-octyl-N-(2,2,6,6-tetramethylpiperid-4-yl)amino]-1,3,5-triazin-6-yl)amino]-4-[N-(2,4-bis[N-octyl-N-(2,2,6,6-tetramethylpiperid-4-yl)amino]-1,3,5-triazin-6-yl)aminomethyl]octane

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A solution of 28.3 g of 2-chloro-4,6-bis[N-octyl-N-(2,2,6,6-tetramethyl-4-piperidyl)amino]-1,3,5-triazine [prepared as described in Preparation 2(b)] and 1.0 g of 1,8-diamino-4-aminomethyloctane in 200 ml of xylene was refluxed for 10 hours. It was then treated as described in Example 1 to give a residue, which was purified by column chromatography through silica gel, eluted with a 20:1:1 by volume mixture of ethyl acetate, ethanol and triethylamine, to give the desired Compound No. 14, in the form of crystals melting at 55°-60° C.

Workup

  1. additionIt was then treated
  2. customto give a residue, which
  3. customwas purified by column chromatography through silica gel
  4. washeluted with a 20:1:1 by volume mixture of ethyl acetate, ethanol and triethylamine

Sources & evidence

ORD record
ord-fc11622d210a480482bbbb75972badda
Source dataset
uspto-grants-1985_08
Patent number
US04533688

Reaction notes

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