Dimethylcarbamoyl Chloride → tert-Butyl 4-(dimethylcarbamoyl)piperazine-1-carboxylate

HRID 2304251Notes

Reaction equation

HRID 2304251 reaction equation
[CH3:1][C:2]([CH3:13])([O:4][C:5]([N:7]1[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]1)=[O:6])[CH3:3].[CH3:14][N:15]([CH3:19])[C:16](Cl)=[O:17].C(=O)([O-])O.[Na+]>ClCCl.C(N(CC)CC)C>[CH3:3][C:2]([CH3:13])([O:4][C:5]([N:7]1[CH2:8][CH2:9][N:10]([C:16]([N:15]([CH3:19])[CH3:14])=[O:17])[CH2:11][CH2:12]1)=[O:6])[CH3:1]

Participants

6

Reactant 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 143452tert-Butyl piperazine-1-carboxylateHCID 516892Sodium Bicarbonate

Product 1

HCID 22665738tert-Butyl 4-(dimethylcarbamoyl)piperazine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Procedure

To a solution of 1.92 g 1-(1,1-dimethylethyloxycarbonyl)piperazine in 11 mL of dichloromethane and 1.5 mL of triethylamine at room temperature was added dropwise 1 mL of dimethylcarbamylchloride. After 16 hours 5% aqueous sodium hydrogencarbonate and dichloromethane were added, the organic layer separated, dried over magnesium sulfate and concentrated. Column chromatography on silica gel (dichloromethane/methanol=95/5 v/v) yielded 1.34 g 1-(1,1-dimethylethyloxycarbonyl)-4-(dimethylaminocarbonyl)piperazine. This compound was dissolved in a 3N hydrogen chloride solution in methanol at 0° C. After 15 min the reaction mixture was allowed to warm to room temperature and After stirring for 3 days at room temperature the reaction mixture was concentrated to give 1.06 g of 1-(dimethylaminocarbonyl)piperazine hydrochloride. rf=0.29, SiO2:dichloromethane/methanol=4/1 v/v.

Workup

  1. customthe organic layer separated
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-cfaa8e0bd1044ea3b18fc7a98d3c141e
Source dataset
uspto-grants-2002_08
Patent number
US06432955B1

Reaction notes

Loading…