Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → tert-Butyl 4-(3-hydroxyphenyl)piperazine-1-carboxylate

HRID 856111Notes

Reaction equation

HRID 856111 reaction equation
O1CCCCC1[O:7][C:8]1[CH:9]=[C:10]([N:14]2[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]2)[CH:11]=[CH:12][CH:13]=1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>C(O)C>[OH:7][C:8]1[CH:9]=[C:10]([N:14]2[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]2)[CH:11]=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 23081281Tert-butyl 4-[3-(tetrahydropyran-2-yloxy)phenyl]piperazine-1-carboxylate

Product 1

HCID 18669061tert-Butyl 4-(3-hydroxyphenyl)piperazine-1-carboxylateYield 93.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of tert-butyl 4-[3-(tetrahydropyran-2-yloxy)phenyl]piperazine-1-carboxylate (5.20 g, 14.4 mmol) prepared in Reference Example 199 and a catalytic amount of pyridinium p-toluene sulfonate in ethanol (100 ml) was stirred at 70° C. for 1.5 hours. The reaction mixture was concentrated under reduced pressure, and methylene chloride and a saturated sodium hydrogencarbonate aqueous solution were added to the residue, which was stirred for a while. The resulting precipitates were collected by filtrasion, and then dried in vacuo to afford tert-butyl 4-(3-hydroxyphenyl)piperazine-1-carboxylate (3.73 g, yield 93%) as a a pale brown powder.

Workup

  1. customprepared in Reference Example 199
  2. concentrationThe reaction mixture was concentrated under reduced pressure, and methylene chloride
  3. additiona saturated sodium hydrogencarbonate aqueous solution were added to the residue, which
  4. customThe resulting precipitates
  5. customwere collected by filtrasion
  6. customdried in vacuo

Sources & evidence

ORD record
ord-d51dbb5483d846bb910089a0e3c27698
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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