Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → Tert-butyl 4-(2-chloro-4-hydroxyphenyl)-piperazine-1-carboxylate

HRID 856106Notes

Reaction equation

HRID 856106 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([O:8]C2CCCCO2)[CH:5]=[CH:4][C:3]=1[N:15]1[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17][CH2:16]1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>C(O)C>[Cl:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[N:15]1[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17][CH2:16]1

Participants

4

Reactant 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 23081313Tert-butyl 4-[2-chloro-4-(tetrahydropyran-2-yloxy)phenyl]piperazine-1-carboxylate

Product 1

HCID 23081264Tert-butyl 4-(2-chloro-4-hydroxyphenyl)-piperazine-1-carboxylateYield 72%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of tert-butyl 4-[2-chloro-4-(tetrahydropyran-2-yloxy)phenyl]piperazine-1-carboxylate (4.73 g, 11.9 mmol) prepared in Reference Example 193 and a catalytic amount of pyridinium p-toluene sulfonate in ethanol (50 ml) was stirred at 70° C. for 1 hour. The reaction mixture was concentrated under reduced pressure, and methylene chloride and saturated sodium hydrogencarbonate aqueous solution were added to the residue, which was stirred for a while. The resulting precipitates were collected by filtration, and dried in vacuo to afford tert-butyl 4-(2-chloro-4-hydroxyphenyl)piperazine-1-carboxylate (2.68 g, yield 72%) as a white powder.

Workup

  1. customprepared in Reference Example 193
  2. concentrationThe reaction mixture was concentrated under reduced pressure, and methylene chloride and saturated sodium hydrogencarbonate aqueous solution
  3. additionwere added to the residue, which
  4. customThe resulting precipitates
  5. filtrationwere collected by filtration
  6. customdried in vacuo

Sources & evidence

ORD record
ord-fb93f9c5a7864906b81d5ded434564a8
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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