Acetyl chloride → HCID 23441041, compound

HRID 2119365Notes

Reaction equation

HRID 2119365 reaction equation
[OH:1][C:2]([C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([OH:24])[CH:19]=1)([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:3][CH2:4][N:5]1[CH2:11][CH2:10][CH2:9][NH:8][CH2:7][CH2:6]1.[C:25](Cl)(=[O:27])[CH3:26].CCN(CC)CC.C([O-])(O)=O.[Na+]>CC#N>[C:25]([N:8]1[CH2:9][CH2:10][CH2:11][N:5]([CH2:4][CH2:3][C:2]([OH:1])([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([OH:24])[CH:19]=2)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:6][CH2:7]1)(=[O:27])[CH3:26]

Participants

6

Reactant 4

HCID 6367Acetyl chloride2×HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 23441016HCID 23441016, compound2×

Product 1

HCID 23441041HCID 23441041, compoundYield 18%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Compound No. 296 (16 mg, 18%) was prepared from 1-[3-hydroxy-3-(3-hydroxyphenyl)-3-phenylpropyl]homopiperazine (Compound No. 295, 78 mg, 0.24 mmol) and acetyl chloride (19 mg, 1.0 equiv). Acetyl chloride and Et3N (121 mg, 1.2 mmol, 5.0 equiv) were added to a solution of 1-[3-hydroxy-3-(3-hydroxyphenyl)-3-phenylpropyl]homopiperazine (Compound No. 295) in CH3CN (2.0 mL). The reaction mixture was stirred at room temperature for 30 min. saturated aqueous NaHCO3 (10 mL) was added to the reaction mixture and the mixture was extracted with AcOEt (3×15 mL). The combined extracts were dried over MgSO4. The solvent was removed under reduced pressure to afford an oil which was purified by column chromatography (SiO2, 3-10% CH3OH/CH2Cl2) to give 1-acetyl-4-[3-hydroxy-3-(3-hydroxyphenyl)-3-phenylpropyl]homopiperazine (Compound No. 296): 16 mg, 18% yield, colorless oil: RPLC tR=4.75 min (89%), 220 nm (Method B); ESI/MS m/e 369.3 (M++H, C22H29N2O3).

Workup

  1. additionwas added to the reaction mixture
  2. extractionthe mixture was extracted with AcOEt (3×15 mL)
  3. dry with materialThe combined extracts were dried over MgSO4
  4. customThe solvent was removed under reduced pressure
  5. customto afford an oil which
  6. customwas purified by column chromatography (SiO2, 3-10% CH3OH/CH2Cl2)

Sources & evidence

ORD record
ord-976099bc5f944908a9161283332c4413
Source dataset
uspto-grants-2004_02
Patent number
US06686353B1

Reaction notes

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