Triethylamine → HCID 53255592, compound

HRID 751646Notes

Reaction equation

HRID 751646 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([NH2:14])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[N+:22]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[S:31](Cl)(=[O:33])=[O:32])([O-:24])=[O:23]>ClCCl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][S:31]([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=2[N+:22]([O-:24])=[O:23])(=[O:32])=[O:33])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 155402-Nitrobenzenesulfonyl chlorideHCID 12682914-Amino-1-Boc-piperidine

Product 1

HCID 53255592HCID 53255592, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-aminopiperidine-1-carboxylic acid tert-butyl ester (400 mg, 200 mmol) in anhydrous dichloromethane (14 mL) under argon was added triethylamine (340 μL, 2.4 mmol) and the solution cooled in an ice bath. 2-Nitrophenylsulfonyl chloride (443 mg, 2.0 mmol) was added and the reaction allowed to stir at rt for 16 h. The crude solution was washed with water (2×30 mL) before removing the solvent in vacuo. The crude material was purified by chromatography using ethyl acetate/petroleum ether (30–60%) as the eluent to give the title compound as an off-white powder. δH (d6 DMSO): 8.43 (2H, m), 8.17 (1H, s), 8.09 (2H, m), 3.80–3.69 (2H, m), 3.31–3.23 (1H, m), 2.86–2.69 (2H, m), 1.63–1.51 (2H, m), 1.39 (9H, s), 1.29–1.17 (2H, m).

Workup

  1. temperaturethe solution cooled in an ice bath
  2. washThe crude solution was washed with water (2×30 mL)
  3. custombefore removing the solvent in vacuo
  4. customThe crude material was purified by chromatography

Sources & evidence

ORD record
ord-f053bcf79f42459e98076d9f13236de8
Source dataset
uspto-grants-2008_07
Patent number
US07405210B2

Reaction notes

Loading…