Triethylamine → HCID 54592563, compound

HRID 1772786Notes

Reaction equation

HRID 1772786 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][CH:22]([CH3:26])[C:23](Cl)=[O:24]>C(Cl)Cl>[Cl:21][CH:22]([CH3:26])[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 8471TriethylamineHCID 1110192-Chloropropionyl chlorideHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 54592563HCID 54592563, compoundYield 101%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of tert-butyl piperazine-1-carboxylate (2.0 g, 11 mmol) in methylene chloride (20 mL) was added triethylamine (3.0 mL, 21 mmol) followed by 2-chloropropanoyl chloride (1.5 g, 12 mmol) drop-wise at 0° C. The reaction was stirred for 1 h, quenched with water, and extracted with dichloromethane. The combined organic layers were washed with water, brine, dried over magnesium sulfate and then evaporated to dryness to provide the crude product (3 g, 101%). LCMS calculated for C8H14ClN2O3 (M-Bu+H)+: m/z=221.1; Found: 221.1.

Workup

  1. customquenched with water
  2. extractionextracted with dichloromethane
  3. washThe combined organic layers were washed with water, brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-4ff0c7cf94214faa9e89e6fcdb4829fa
Source dataset
uspto-grants-2016_02
Patent number
US09249145B2

Reaction notes

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