3,4,5-Trimethoxybenzylamine → Piperazine, 1-(4-chloro-3-(trifluoromethyl)phenyl)-4-((3,4,5-trimethoxyphenyl)methyl)-, monohydrochloride

HRID 1164484Notes

Reaction equation

HRID 1164484 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]1[CH:4]=[C:5]([N:10]([CH2:14][CH2:15]Cl)[CH2:11][CH2:12]Cl)[CH:6]=[CH:7][C:8]=1[Cl:9].[CH3:19][O:20][C:21]1[CH:22]=[C:23]([CH:26]=[C:27]([O:31][CH3:32])[C:28]=1[O:29][CH3:30])[CH2:24][NH2:25]>[OH-].[Na+]>[ClH:9].[CH3:32][O:31][C:27]1[CH:26]=[C:23]([CH:22]=[C:21]([O:20][CH3:19])[C:28]=1[O:29][CH3:30])[CH2:24][N:25]1[CH2:15][CH2:14][N:10]([C:5]2[CH:6]=[CH:7][C:8]([Cl:9])=[C:3]([C:2]([F:18])([F:17])[F:1])[CH:4]=2)[CH2:11][CH2:12]1

Participants

4

Reactant 2

HCID 877363,4,5-TrimethoxybenzylamineHCID 20511242HCID 20511242, compound

Product 1

HCID 3062152Piperazine, 1-(4-chloro-3-(trifluoromethyl)phenyl)-4-((3,4,5-trimethoxyphenyl)methyl)-, monohydrochlorideYield 148.5%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

3.23 g of N-(3-trifluoromethyl-4-chlorophenyl)-N,N-bis-(2-chloroethyl)-amine and 7 g of 3,4,5-trimethoxybenzyl amine are heated to 120° C. under N2 atmosphere for 8 hours. After cooling of the reaction mixture 50 ml of 1 N NaOH is added, excess 3,4,5-trimethoxybenzyl amine being removed by distillation by steam. After evaporation of the residue to dryness it is mixed with methanol, and hydrochloric acid gas is introduced in the solution. After sucking off and drying the resulting precipitate, 3.6 g of N-(3,4,5-trimethoxy-benzyl)-N'-(3-trifluoromethyl-4-chlorophenyl)-piperazine hydrochloride is obtained.

Workup

  1. additionis added
  2. customexcess 3,4,5-trimethoxybenzyl amine being removed by distillation by steam
  3. customAfter evaporation of the residue to dryness it
  4. additionis mixed with methanol, and hydrochloric acid gas
  5. additionis introduced in the solution
  6. customdrying the resulting precipitate

Sources & evidence

ORD record
ord-c34cade4c2974d0ab953a9f94cd23875
Source dataset
uspto-grants-1983_01
Patent number
US04370329

Reaction notes

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