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

HRID 431524Notes

Reaction equation

HRID 431524 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 mml) 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%). 1H-NMR (CDCl3): δ (s, 9H, 1.4), (m, 4H, 3.07), (m, 4H, 3.55), (dd, 1H, 7.55, J=1,12), (dd, 1H, 7.75, J=1,12), (m, 4H, 7.9), (s, 1H, 8.3), MS (FD) 410.1 M+; IR (chloroform) carbonyl 1691 cm−1. Anal. Calcd: C, 55.54; H, 5.64; N, 6.82; Cl, 8.63; Found: C, 55.71; H, 5.76; N, 6.85; Cl, 8.76.

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-aaf8b4daa3a5494da5ceaacf6dce409b
Source dataset
uspto-grants-2003_12
Patent number
US06660739B1

Reaction notes

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