Triethylamine → HCID 69410613, compound

HRID 1592754Notes

Reaction equation

HRID 1592754 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[NH2:20])[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C(N(CC)CC)C.[CH2:28]([S:30](Cl)(=[O:32])=[O:31])[CH3:29]>C(Cl)Cl.C(OCC)(=O)C>[C:1]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[NH:20][S:30]([CH2:28][CH3:29])(=[O:32])=[O:31])[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 11667Ethanesulfonyl chlorideHCID 2795530tert-Butyl 4-(2-aminophenyl)piperazine-1-carboxylate

Product 1

HCID 69410613HCID 69410613, compoundYield 45%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1.0 g (4.4 mmol) of 1-Boc-4-(2-amino-phenyl)-piperazine and 1.1 mL (6.6 mmol) of triethylamine in 12 mL of DCM was added 0.63 mL (6.6 mmol) of ethanesulfonyl chloride, and the mixture was stirred at r.t. for about 16 hours. The mixture was diluted with ethyl acetate and washed once with 10% aqueous sodium bisulfate and then once with saturated aqueous sodium bicarbonate. The organic portion was dried (Na2SO4), filtered and concentrated in vacuo. Silica gel chromatography (3iotage, 40% ethyl acetate/hexanes) of the residue afforded about 0.73 g (45%) of the title compound. LRMS (ESI−): 368 (M−1)

Workup

  1. washwashed once with 10% aqueous sodium bisulfate
  2. dry with materialThe organic portion was dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-86d76aff8f08474e90de19d0a1016952
Source dataset
uspto-grants-2007_11
Patent number
US07291619B2

Reaction notes

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