Triethylamine → 4-tert-Butoxycarbonyl-1-[(3-chloro-1-propyl)sulfonyl]piperazine

HRID 2365185Notes

Reaction equation

HRID 2365185 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][CH2:22][CH2:23][CH2:24][S:25](Cl)(=[O:27])=[O:26]>C(Cl)(Cl)Cl>[C:4]([O:3][C:1]([N:8]1[CH2:9][CH2:10][N:11]([S:25]([CH2:24][CH2:23][CH2:22][Cl:21])(=[O:27])=[O:26])[CH2:12][CH2:13]1)=[O:2])([CH3:7])([CH3:6])[CH3:5]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 154103-Chloropropanesulphonyl chlorideHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 227098904-tert-Butoxycarbonyl-1-[(3-chloro-1-propyl)sulfonyl]piperazine

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 1-BOC-piperazine (3.26 g) and triethylamine (2.68 mL) in dry chloroform (25 mL) was added 3-chloropropanesulfonyl chloride (2.62 g) at 0° C. After 2 h wash with water, dry (Na2SO4), filter and concentrate to give crude material. Product was isolated by flash chromatography (95%).

Workup

  1. washAfter 2 h wash with water
  2. dry with materialdry (Na2SO4)
  3. filtrationfilter
  4. concentrationconcentrate
  5. customto give crude material
  6. customProduct was isolated by flash chromatography (95%)

Sources & evidence

ORD record
ord-4f743f1f3d024f60babc69283b70dfb9
Source dataset
uspto-grants-2014_04
Patent number
US08697693B2

Reaction notes

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