Chloroacetyl chloride → Tert-butyl 4-(2-chloroacetyl)piperazine-1-carboxylate

HRID 2036183Notes

Reaction equation

HRID 2036183 reaction equation
[N:1]1([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[Cl:21][CH2:22][C:23](Cl)=[O:24]>ClCCl>[Cl:21][CH2:22][C:23]([N:4]1[CH2:5][CH2:6][N:1]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:2][CH2:3]1)=[O:24]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 15829156Tert-butyl 4-(2-chloroacetyl)piperazine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
3 °C

Procedure

2.00 g (10.74 mmol) tert-butyl 1-piperazinecarboxylate, 1.30 g (12.89 mmol, 1.2 eq.) triethylamine were dissolved into 25 ml dichloromethan under argon gas. After cooling to 3° C., 1.33 g (11.81 mmol, 1.1 eq.) chloroacetyl chloride was diluted with 5 ml dichloromethane and added dropwise slowly into reaction solution. After stirring at 3° C. for 1 hour, 20 ml purified water was added, organic layer was separated and aqueous layer was extracted once with 40 ml dichloromethane again. Organic layer was collected, dried with magnesium sulfate and concentrated with decompression. Purifying residues by chromatography using silicagel, 2.00 g (71%) target compound as yellow syrup was yielded.

Workup

  1. additionadded dropwise slowly into reaction solution
  2. custom20 ml purified water
  3. additionwas added
  4. customorganic layer was separated
  5. extractionaqueous layer was extracted once with 40 ml dichloromethane again
  6. customOrganic layer was collected
  7. dry with materialdried with magnesium sulfate
  8. concentrationconcentrated with decompression
  9. custom2.00 g (71%) target compound as yellow syrup was yielded

Sources & evidence

ORD record
ord-360212c244534889bda6e188117edf03
Source dataset
uspto-grants-2013_11
Patent number
US08575173B2

Reaction notes

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