Acetyl chloride → HCID 66649177, compound

HRID 418685Notes

Reaction equation

HRID 418685 reaction equation
[F:1][C:2]1[CH:23]=[C:22]([N+:24]([O-:26])=[O:25])[CH:21]=[CH:20][C:3]=1[O:4][C:5]1[CH:10]=[CH:9]N=[C:7]2[CH:11]=[C:12]([C:14]3[CH2:15][CH2:16][NH:17][CH2:18][CH:19]=3)[S:13][C:6]=12.[CH3:27]CN(C(C)C)C(C)C.[C:36](Cl)(=[O:38])[CH3:37]>C(Cl)Cl>[F:1][C:2]1[CH:23]=[C:22]([N+:24]([O-:26])=[O:25])[CH:21]=[CH:20][C:3]=1[O:4][C:5]1[C:6]2[S:13][C:12]([C:14]3[CH2:15][CH2:16][N:17]([C:36](=[O:38])[CH3:37])[CH2:18][CH:19]=3)=[CH:11][C:7]=2[CH:27]=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 81531DiisopropylethylamineHCID 59457731HCID 59457731, compound

Product 1

HCID 66649177HCID 66649177, compoundYield 80.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 4-(7-(2-fluoro-4-nitrophenoxy)benzo[b]thiophen-2-yl)-1,2,3,6-tetrahydropyridine 268 (400 mg, 1.08 mmol) and DIPEA (0.207 mL, 1.19 mmol) in DCM was added acetyl chloride (0.15 mL, 2.16 mmol) at room temperature and the mixture (that turned homogeneous soon after) was stirred for 1 h. The crude mixture was concentrated under reduced pressure and the residue purified by flash chromatography (5% MeOH to 10% MeOH in DCM) affording 269 (358.2 mg, 0.87 mmol, 80% yield) as a white solid. MS (m/z): (M+1) 414.4 (100%).

Workup

  1. concentrationThe crude mixture was concentrated under reduced pressure
  2. customthe residue purified by flash chromatography (5% MeOH to 10% MeOH in DCM)

Sources & evidence

ORD record
ord-816d9f72d9da40578404e0e4f544ed04
Source dataset
uspto-grants-2012_01
Patent number
US08093264B2

Reaction notes

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