1-Piperazinecarboxylic acid, ethyl ester → 3,6-Difluoro-2-(4-ethoxycarbonyl-1-piperazinyl)-5-nitrobenzyl alcohol

HRID 2107590Notes

Reaction equation

HRID 2107590 reaction equation
[F:1][C:2]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][C:7]([F:13])=[C:6](F)[C:3]=1[CH2:4][OH:5].[CH2:15]([O:17][C:18]([N:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1)=[O:19])[CH3:16].C(N(CC)CC)C>C(O)C.O>[F:13][C:7]1[C:6]([N:23]2[CH2:22][CH2:21][N:20]([C:18]([O:17][CH2:15][CH3:16])=[O:19])[CH2:25][CH2:24]2)=[C:3]([C:2]([F:1])=[C:9]([N+:10]([O-:12])=[O:11])[CH:8]=1)[CH2:4][OH:5]

Participants

6

Reactant 3

HCID 84311-Piperazinecarboxylic acid, ethyl esterHCID 8471TriethylamineHCID 156318292,3,6-Trifluoro-5-nitrobenzenemethanol

Product 1

HCID 156225283,6-Difluoro-2-(4-ethoxycarbonyl-1-piperazinyl)-5-nitrobenzyl alcoholYield 37.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

To a solution of 2,5,6-trifluoro-3-nitrobenzyl alcohol (14 g) in ethanol (64 ml) and water (7 ml) is added a mixture of 4-ethoxycarbonylpiperazine (11 g), triethylamine (12.5 g) and ethanol (18 ml) at one time. The mixture is stirred at room temperature overnight, and the resulting precipitates are separated by filtration. The crystals are washed with a small amount of diethyl ether and recrystallized from ethanol to give 3,6-difluoro-2-(4-ethoxycarbonyl-1-piperazinyl)-5-nitrobenzyl alcohol (8.7 g), as yellow needles, m.p. 147°-149° C.

Workup

  1. customthe resulting precipitates
  2. customare separated by filtration
  3. washThe crystals are washed with a small amount of diethyl ether
  4. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-9574725c0b704975a76985269c3d8295
Source dataset
uspto-grants-1990_06
Patent number
US04935420

Reaction notes

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