Acetyl chloride → HCID 59485112, compound

HRID 1850517Notes

Reaction equation

HRID 1850517 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:14][CH2:13][N:12]([C:15]3[C:16]([CH3:29])=[C:17]([CH3:28])[C:18]4[O:22][C:21]([CH2:24][NH2:25])([CH3:23])[CH2:20][C:19]=4[C:26]=3[CH3:27])[CH2:11][CH2:10]2)=[CH:5][CH:4]=1.C(N(CC)CC)C.[C:37](Cl)(=[O:39])[CH3:38]>O.C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([N:9]2[CH2:10][CH2:11][N:12]([C:15]3[C:16]([CH3:29])=[C:17]([CH3:28])[C:18]4[O:22][C:21]([CH2:24][NH:25][C:37](=[O:39])[CH3:38])([CH3:23])[CH2:20][C:19]=4[C:26]=3[CH3:27])[CH2:13][CH2:14]2)=[CH:7][CH:8]=1

Participants

6

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 59484990HCID 59484990, compound

Product 1

HCID 59485112HCID 59485112, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of THF (2.0 mL) containing 1-{5-[4-(4-Methoxyphenyl)piperazin-1-yl]-2,4,6,7-tetramethyl-2,3-dihydro-1-benzofuran-2-yl}methaneamine (110 mg, 0.278 mmol) synthesized in Example 108, triethylamine (42 mg, 0.417 mmol) and acetylchloride (26 mg, 0.337 mmol) were serially added under ice-cooling condition, and the mixture was stirred at 0° C. for 30 minutes. The reaction solution was diluted with water, and THF was removed under reduced pressure, followed by extraction using ethyl acetate. The extract was washed with saturated saline and dried using anhydrous magnesium sulfate. After that, the solvent was removed under reduced pressure. The obtained residue was purified by silica gel chromatography (hexane-ethyl acetate 7:3-3:7) and crystallized from ethyl acetate-hexane to obtain 90 mg of the title compound (yield 74%). Melting point was 146 to 152° C.

Workup

  1. additionwere serially added under ice-
  2. temperaturecooling condition
  3. customwas removed under reduced pressure
  4. extractionfollowed by extraction
  5. washThe extract was washed with saturated saline
  6. customdried
  7. customAfter that, the solvent was removed under reduced pressure
  8. customThe obtained residue was purified by silica gel chromatography (hexane-ethyl acetate 7:3-3:7)
  9. customcrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-073aaec480ba46b992c30f9b3c6614c0
Source dataset
uspto-grants-2015_02
Patent number
US08957069B2

Reaction notes

Loading…