Triethylamine → HCID 19841171, compound

HRID 1073154Notes

Reaction equation

HRID 1073154 reaction equation
[CH3:1][CH:2]1[NH:7][CH2:6][CH2:5][N:4]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:3]1.[C:15]([C:18]1[CH:23]=[C:22]([Cl:24])[C:21]([NH:25][C:26](=[O:29])[CH2:27]Cl)=[C:20]([Cl:30])[CH:19]=1)(=[O:17])[CH3:16].C(N(CC)CC)C>CN(C)C=O>[C:15]([C:18]1[CH:19]=[C:20]([Cl:30])[C:21]([NH:25][C:26](=[O:29])[CH2:27][N:7]2[CH2:6][CH2:5][N:4]([C:8]([O:10][C:11]([CH3:13])([CH3:12])[CH3:14])=[O:9])[CH2:3][CH:2]2[CH3:1])=[C:22]([Cl:24])[CH:23]=1)(=[O:17])[CH3:16]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2756810tert-Butyl 3-methylpiperazine-1-carboxylateHCID 15087743HCID 15087743, compound

Product 1

HCID 19841171HCID 19841171, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 12 parts of (1,1-dimethylethyl) 3-methyl-1-piperazinecarboxylate, 18.7 parts of N-(4-acetyl-2,6-dichlorophenyl)-2-chloroacetamide, 11.8 parts of N,N-diethylethanamine and 230 parts of N,N-dimethylformamide was stirred first for 8 hours at 70° C. and then over weekend at room temperature. The reaction mixture was evaporated and the residue was taken up in water. The product was extracted twice with dichloromethane. The combined extracts were washed with water, dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using trichloromethane as eluent. The desired fraction was collected and the eluent was evaporated, yielding 27 parts (100%) of (1,1-dimethylethyl) 4-[2-[(4-acetyl-2,6-dichlorophenyl)amino]-2-oxoethyl]-3-methyl-1-piperazinecarboxylate as a residue (int. 21).

Workup

  1. waitover weekend at room temperature
  2. customThe reaction mixture was evaporated
  3. extractionThe product was extracted twice with dichloromethane
  4. washThe combined extracts were washed with water
  5. customdried
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified by column chromatography over silica gel
  9. customThe desired fraction was collected
  10. customthe eluent was evaporated

Sources & evidence

ORD record
ord-f6877288bf864cf98d6de8a55c1dc4fd
Source dataset
uspto-grants-1990_11
Patent number
US04968684

Reaction notes

Loading…