Acetyl chloride → HCID 58786545, compound

HRID 1376047Notes

Reaction equation

HRID 1376047 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH:14]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[F:24])[CH2:15][NH:16][CH3:17])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:25](Cl)(=[O:27])[CH3:26].C(N(CC)CC)C>C(Cl)Cl.S(=O)(=O)(O)[O-].[Na+]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH:14]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[F:24])[CH2:15][N:16]([C:25](=[O:27])[CH3:26])[CH3:17])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 6367Acetyl chloride2×HCID 8471TriethylamineHCID 58786487HCID 58786487, compound

Product 1

HCID 58786545HCID 58786545, compoundYield 16%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 516919Sodium BisulfateSolvent

Conditions

Temperature
0 °C

Procedure

To 4-[1-(2-Fluoro-phenyl)-2-methylamino-ethyl]-piperazine-1-carboxylic acid tert-butyl ester (425) (0.95 g, 2.81 mmol) in MeCl2(10 mL) was added TEA (0.43 mL, 3.10 mmol). The solution was cooled to 0° C. and allowed to stir for 15 min. Acetyl chloride (0.20 mL, 2.81 mmol) was then added. The reaction was allowed to stir at 0° C. for 35 min and then at room temperature for 132 h. Additional triethylamine (0.39 mL, 2.81 mmol), and acetyl chloride (0.2 mL, 2.81 mmol) were added. The reaction mixture was then diluted with 10% aq. sodium bisulfate (20 mL). The organic layer was separated and the aqueous portion was extracted with dichloromethane (3×). The organics are combined, dried with sodium sulfate and concentrated to dryness. The crude material was purified by chromatography (silica gel 60 mesh, eluting with 2% (2M NH3 in MeOH) in MeCl2) yielding 0.17 g (16%) pure product.

Workup

  1. stirringto stir at 0° C. for 35 min
  2. waitat room temperature for 132 h
  3. customThe organic layer was separated
  4. extractionthe aqueous portion was extracted with dichloromethane (3×)
  5. dry with materialdried with sodium sulfate
  6. concentrationconcentrated to dryness
  7. customThe crude material was purified by chromatography (silica gel 60 mesh, eluting with 2% (2M NH3 in MeOH) in MeCl2)

Sources & evidence

ORD record
ord-3eaae76cd63646e0b3beae3bc7f775ea
Source dataset
uspto-grants-2007_01
Patent number
US07169777B2

Reaction notes

Loading…