Benzenemethanol, 4-amino-alpha-(aminomethyl)-3,5-dichloro- → 4-Amino-3,5-dichloro-alpha-[[[6-[[6-(pyrazinyl)hexyl]oxy]hexyl]amino]methyl]benzenemethanol

HRID 982401Notes

Reaction equation

HRID 982401 reaction equation
[NH2:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([CH:9]([CH2:11][NH2:12])[OH:10])=[CH:4][C:3]=1[Cl:13].Br[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][O:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][C:28]1[CH:33]=[N:32][CH:31]=[CH:30][N:29]=1>CN(C=O)C>[NH2:1][C:2]1[C:3]([Cl:13])=[CH:4][C:5]([CH:9]([CH2:11][NH:12][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][O:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][C:28]2[CH:33]=[N:32][CH:31]=[CH:30][N:29]=2)[OH:10])=[CH:6][C:7]=1[Cl:8]

Participants

4

Reactant 2

HCID 217242Benzenemethanol, 4-amino-alpha-(aminomethyl)-3,5-dichloro-HCID 19876745[6-[(6-Bromohexyl)oxy]hexyl]pyrazine

Product 1

HCID 198767424-Amino-3,5-dichloro-alpha-[[[6-[[6-(pyrazinyl)hexyl]oxy]hexyl]amino]methyl]benzenemethanolYield 56.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-amino-α-(aminomethyl)-3,5-dichlorobenzenemethanol (1.2 g), DEA (0.72 ml) and [6-[(6-bromohexyl)oxy]hexyl]pyrazine (1.16 g) in DMF (10 ml) was heated at 100°-110° for 3 h. The resulting dark solution was evaporated in vacuo and the residue purified by FCC eluting with System B (96:2:2→93:5:2) to give the title compound as pale yellow crystals (0.92 g), m.p. 60°-63°.

Workup

  1. customThe resulting dark solution was evaporated in vacuo
  2. customthe residue purified by FCC
  3. washeluting with System B (96:2:2→93:5:2)

Sources & evidence

ORD record
ord-4365100c8a7b4703a42430fe8a119d1a
Source dataset
uspto-grants-1991_02
Patent number
US04996218

Reaction notes

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