Triethylamine → 1-Boc-4-(6-chloronaphthalen-2-ylsulfonyl)piperazine

HRID 1372881Notes

Reaction equation

HRID 1372881 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C(N(CC)CC)C.[Cl:21][C:22]1[CH:23]=[C:24]2[C:29](=[CH:30][CH:31]=1)[CH:28]=[C:27]([S:32](Cl)(=[O:34])=[O:33])[CH:26]=[CH:25]2>C(Cl)Cl>[C:1]([N:8]1[CH2:9][CH2:10][N:11]([S:32]([C:27]2[CH:26]=[CH:25][C:24]3[C:29](=[CH:30][CH:31]=[C:22]([Cl:21])[CH:23]=3)[CH:28]=2)(=[O:33])=[O:34])[CH2:12][CH2:13]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 106351296-Chloronaphthalene-2-sulfonyl chloride

Product 1

HCID 187613901-Boc-4-(6-chloronaphthalen-2-ylsulfonyl)piperazine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirring solution of N-Boc-piperazine (400 mg, 2.1 mmol) and triethylamine (1 mL, 7 mmol) in methylene chloride (5 mL) was added 6-chloro-2-naphthalenesulfonyl chloride (500 mg, 1.9 mmol). After 2 h the solution was washed with water, dried over sodium sulfate and evaporated. The residue was chromatographed on a (Biotage) silica column, eluting with ethyl acetate:hexanes (2:8), to give 300 mg (38%).

Workup

  1. washAfter 2 h the solution was washed with water
  2. dry with materialdried over sodium sulfate
  3. customevaporated
  4. customThe residue was chromatographed on a (Biotage) silica column
  5. washeluting with ethyl acetate:hexanes (2:8)
  6. customto give 300 mg (38%)

Sources & evidence

ORD record
ord-68448ca652404fe78b6cca3aa467ecd5
Source dataset
uspto-grants-2007_01
Patent number
US07160878B2

Reaction notes

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