Acetyl chloride → 1-(4-Fluorophenethylpiperdin-4-yl]-6-acetamidomethylindoline

HRID 1790449Notes

Reaction equation

HRID 1790449 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[F:5][C:6]1[CH:30]=[CH:29][C:9]([CH2:10][CH2:11][N:12]2[CH2:17][CH2:16][CH:15]([N:18]3[C:26]4[C:21](=[CH:22][CH:23]=[C:24]([CH2:27][NH2:28])[CH:25]=4)[CH2:20][CH2:19]3)[CH2:14][CH2:13]2)=[CH:8][CH:7]=1.C(N(CC)CC)C.[OH-].[Na+]>C(#N)C.O>[F:5][C:6]1[CH:30]=[CH:29][C:9]([CH2:10][CH2:11][N:12]2[CH2:13][CH2:14][CH:15]([N:18]3[C:26]4[C:21](=[CH:22][CH:23]=[C:24]([CH2:27][NH:28][C:1](=[O:3])[CH3:2])[CH:25]=4)[CH2:20][CH2:19]3)[CH2:16][CH2:17]2)=[CH:8][CH:7]=1

Participants

7

Reactant 4

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 220380351-[1-(4-Fluorophenethyl)piperidin-4-yl]-6-aminomethylindoline

Product 1

HCID 100007861-(4-Fluorophenethylpiperdin-4-yl]-6-acetamidomethylindolineYield 54%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

Under ice cooling, acetyl chloride (6.6 ml) was added dropwise into a solution of 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-aminomethylindoline (30 g) obtained above and triethylamine (9.4 g) in acetonitrile (500 ml) and the resultant mixture was stirred at room temperature for 1 hr. After adding a 5 N aqueous solution (40 ml) of sodium hydroxide and water (500 ml) to the reaction solution, the resulting crystalline precipitates were collected by filtration, washed successively with water and ethyl acetate and then dried at 50° C. overnight to give the crude title compound (22.8 g). This crude product was recrystallized successively from ethyl acetate and ethanol to give the title compound (17.9 g) as white needles (yield: 54%).

Workup

  1. customthe resulting crystalline precipitates
  2. filtrationwere collected by filtration
  3. washwashed successively with water and ethyl acetate
  4. customdried at 50° C. overnight
  5. customto give the crude title compound (22.8 g)
  6. customThis crude product was recrystallized successively from ethyl acetate and ethanol

Sources & evidence

ORD record
ord-6456d55eb9c6470e9ebbb30f543165a7
Source dataset
uspto-grants-2006_07
Patent number
US07071201B2

Reaction notes

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