Methanol → HCID 18542728, compound

HRID 1268173Notes

Reaction equation

HRID 1268173 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:21]=[CH:20][C:18]([NH2:19])=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].N1C=CC=CC=1.[CH2:28]([S:30](Cl)(=[O:32])=[O:31])[CH3:29].CO>ClCCl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:21]=[CH:20][C:18]([NH:19][S:30]([CH2:28][CH3:29])(=[O:32])=[O:31])=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 887MethanolHCID 1049PyridineHCID 11667Ethanesulfonyl chlorideHCID 22181157tert-Butyl 4-(4-aminophenoxy)piperidine-1-carboxylate

Product 1

HCID 18542728HCID 18542728, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(1-t-butoxycarbonylpiperidin-4-yloxy)aniline (10.6 g) and pyridine (8 ml) in dichloromethane (75 ml) was added dropwise ethanesulfonyl chloride (4.1 ml) in an ice bath and the mixture was stirred at room temperature for 5 hours. After addition of methanol (1 ml), the reaction mixture was concentrated in vacuo. The residue was purified by chromatography on a silica gel column using hexane/ethyl acetate=3/2 as an eluant to give the desired compound (11.7 g, yield 84%) as a pale pink solid.

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. customThe residue was purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-23076e54c06a4f3e98e0687b35f52e4e
Source dataset
uspto-grants-2003_04
Patent number
US06555556B1

Reaction notes

Loading…