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

HRID 2351900Notes

Reaction equation

HRID 2351900 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-a5c3d5f0edb04be2b936a2864bcede68
Source dataset
uspto-grants-1989_10
Patent number
US04874764

Reaction notes

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