Potassium Iodide → 4-(3-Dimethylamino-propane-1-sulfonyl)-piperazine-1-carboxylic acid tert-butyl ester

HRID 253026Notes

Reaction equation

HRID 253026 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([S:14]([CH2:17][CH2:18][CH2:19]Cl)(=[O:16])=[O:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[CH3:22][NH:23][CH3:24].C(=O)([O-])[O-].[K+].[K+].C(N(CC)CC)C.[I-].[K+]>C(#N)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([S:14]([CH2:17][CH2:18][CH2:19][N:23]([CH3:24])[CH3:22])(=[O:16])=[O:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 5

HCID 4875Potassium IodideHCID 8471TriethylamineHCID 10473Dimethylamine, hydrochlorideHCID 11430Potassium CarbonateHCID 227098904-tert-Butoxycarbonyl-1-[(3-chloro-1-propyl)sulfonyl]piperazine

Product 1

HCID 668584634-(3-Dimethylamino-propane-1-sulfonyl)-piperazine-1-carboxylic acid tert-butyl esterYield 111.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 4-(3-chloro-propane-1-sulfonyl)-piperazine-1-carboxylic acid tert-butyl ester (152.6 mg, 0.47 mmol), dimethylamine hydrochloride (403.5 mg, 4.95 mmol, 10.6 eq.), potassium carbonate (72.7 mg, 0.53 mmol, 1.13 eq.) and triethylamine (690 μL, 4.95 mmol, 10.6 eq) in acetonitrile (10 mL) plus a catalytic amount of potassium iodide was heated at 80° C. in a sealed tube overnight. The solvent was then removed in vacuo. The residue diluted with water and extracted with CH2Cl2 (3×20 mL). The combined fractions were dried (Na2SO4) to yield 4-(3-dimethylamino-propane-1-sulfonyl)-piperazine-1-carboxylic acid tert-butyl ester as an orange solid (176 mg).

Workup

  1. customThe solvent was then removed in vacuo
  2. additionThe residue diluted with water
  3. extractionextracted with CH2Cl2 (3×20 mL)
  4. dry with materialThe combined fractions were dried (Na2SO4)

Sources & evidence

ORD record
ord-1e5c27a534864eaf8eb7f9a3c04ca3c7
Source dataset
uspto-grants-2011_01
Patent number
US07872003B2

Reaction notes

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