Triethylamine → HCID 69411481, compound

HRID 1592753Notes

Reaction equation

HRID 1592753 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].CCN(CC)CC.[Cl:28][CH2:29][CH2:30][CH2:31][S:32](Cl)(=[O:34])=[O:33]>C(Cl)Cl>[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:32]([CH2:31][CH2:30][CH2:29][Cl:28])(=[O:34])=[O:33])[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 154103-Chloropropanesulphonyl chlorideHCID 2795530tert-Butyl 4-(2-aminophenyl)piperazine-1-carboxylate

Product 1

HCID 69411481HCID 69411481, compoundYield 93.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-boc-4-(2-amino-phenyl)-piperazine (555 mg, 2.0 mmol) and Et3N (837 uL, 6 mmol) in 20 mL of CH2Cl2 was added 3-chloropropanesulfonyl chloride (255 uL, 2.1 mmol). After stirring for about 30 minutes, the mixture was quenched with saturated aqueous sodium bicarbonate, diluted with EtOAc, washed with 1 M HCl, water and brine, and then dried (Na2SO4), filtered and concentrated. Purification by silica gel chromatography (35 g SiO2, 10 to 30% EtOAc/hexanes, over 30 min at 35 mL/min) afforded about 781 mg (1.87 mmol, 93%) of N-boc-4-[2-(3-chloro-propane-1-sulfonylamino)-phenyl]-piperazine as a white solid. LRMS (ESI+): 418.1 [M+1]

Workup

  1. customthe mixture was quenched with saturated aqueous sodium bicarbonate
  2. additiondiluted with EtOAc
  3. washwashed with 1 M HCl, water and brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by silica gel chromatography (35 g SiO2, 10 to 30% EtOAc/hexanes, over 30 min at 35 mL/min)

Sources & evidence

ORD record
ord-6258873b2bf2483dade7141306e93150
Source dataset
uspto-grants-2007_11
Patent number
US07291619B2

Reaction notes

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