Ammonia → 2,4-Diallylamino-6-{2-[4-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-yl)piperazin-1-yl]ethylamino}-1,3,5-triazine

HRID 2255039Notes

Reaction equation

HRID 2255039 reaction equation
C(O)(=O)/C=C/C(O)=O.C(O)(=O)/C=C/C(O)=O.[CH2:17]([NH:20][C:21]1[N:26]=[C:25]([NH:27][CH2:28][CH:29]=[CH2:30])[N:24]=[C:23]([NH:31][CH2:32][CH2:33][N:34]2[CH2:39][CH2:38][N:37]([CH:40]3[C:46]4[CH:47]=[CH:48][CH:49]=[CH:50][C:45]=4[CH2:44][CH2:43][C:42]4[CH:51]=[CH:52][CH:53]=[CH:54][C:41]3=4)[CH2:36][CH2:35]2)[N:22]=1)[CH:18]=[CH2:19].N>C(O)C.[H][H].[Ni]>[CH2:28]([NH:27][C:25]1[N:26]=[C:21]([NH:20][CH2:17][CH:18]=[CH2:19])[N:22]=[C:23]([NH:31][CH2:32][CH2:33][N:34]2[CH2:35][CH2:36][N:37]([CH:40]3[C:41]4[CH:54]=[CH:53][CH:52]=[CH:51][C:42]=4[CH2:43][CH2:44][C:45]4[CH:50]=[CH:49][CH:48]=[CH:47][C:46]3=4)[CH2:38][CH2:39]2)[N:24]=1)[CH:29]=[CH2:30]

Participants

5

Reactant 2

HCID 222AmmoniaHCID 678577352,4-diallylamino-6-{2-[4-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-yl)piperazin-1-yl]ethylamino}-1,3,5-triazine difumarate

Product 1

HCID 149509122,4-Diallylamino-6-{2-[4-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-yl)piperazin-1-yl]ethylamino}-1,3,5-triazine

Reagents, catalysts & solvents 2

HCID 178506447HCID 178506447, compoundCatalystHCID 702EthanolSolvent

Procedure

When the reaction is complete, the salt is filtered off, the solvent is evaporated and the residue is taken up in ether, washed with water and dried over MgSO4. After evaporation of the ether, the oily residue is chromatographed on 120 g of silica, using the system CH2Cl2 /CH3OH (92/8) as eluant. After evaporation of the eluate, the recovered base is converted into the difumarate in ethanol to yield, ultimately, 7.7 g of 2,4-diallylamino-6-{2-[4-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-yl)piperazin-1-yl]ethylamino}-1,3,5-triazine difumarate crystals melting (cap) at 123°-128° C. The aminoethylpiperazine starting material was prepared by reducing the corresponding cyanomethyl compound, [m.p. (cap): 112°-113° C.] with H2 /Ni, in ethanol, in the presence of NH3.

Workup

  1. filtrationthe salt is filtered off
  2. customthe solvent is evaporated
  3. washwashed with water
  4. dry with materialdried over MgSO4
  5. customAfter evaporation of the ether
  6. customthe oily residue is chromatographed on 120 g of silica
  7. customAfter evaporation of the eluate
  8. customto yield
  9. custom(cap) at 123°-128° C

Sources & evidence

ORD record
ord-3c4625f8dac140a8ae6125b70e51b7a5
Source dataset
uspto-grants-1993_08
Patent number
US05238936

Reaction notes

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