Acetyl chloride → HCID 66967975, compound

HRID 241341Notes

Reaction equation

HRID 241341 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:12][CH:11]([OH:13])[CH:10]([N:14]3[CH2:19][CH2:18][N:17]([C:20]([C:22]4[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=4)=[O:21])[CH2:16][CH2:15]3)[CH2:9]2)=[C:4]([N+:29]([O-:31])=[O:30])[CH:3]=1.CCN(CC)CC.[C:39](Cl)(=[O:41])[CH3:40]>C(Cl)Cl>[Cl:28][C:25]1[CH:26]=[CH:27][C:22]([C:20]([N:17]2[CH2:16][CH2:15][N:14]([CH:10]3[CH2:9][N:8]([C:5]4[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][C:4]=4[N+:29]([O-:31])=[O:30])[CH2:12][CH:11]3[O:13][C:39](=[O:41])[CH3:40])[CH2:19][CH2:18]2)=[O:21])=[CH:23][CH:24]=1

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 58451063HCID 58451063, compound

Product 1

HCID 66967975HCID 66967975, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of {4-[1-(4-chloro-2-nitro-phenyl)-4-hydroxy-pyrrolidin-3-yl]-piperazin-1-yl}-(4-chloro-phenyl)-methanone (300 mg, 0.64 mmol) in CH2Cl2 (5 mL) at 0° C., was added Et3N (0.2 mL, 1.42 mmol) and acetyl chloride (112 mg, 1.42 mmol). The mixture was stirred at RT for overnight. The organic phase was washed with Saturated NaHCO3, dried over Na2SO4, and concentrated. The residue was purified by column chromatography (Ethyl acetate) to give the desired product (160 mg, 50% yield) as a yellow oil. MS: (ESI), M/Z, 507(M+1). Retention time: 2.59 min (FA-polar).

Workup

  1. washThe organic phase was washed with Saturated NaHCO3
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated
  4. customThe residue was purified by column chromatography (Ethyl acetate)

Sources & evidence

ORD record
ord-242b06b4086c499ba8aed0ec38ed888b
Source dataset
uspto-grants-2014_02
Patent number
US08648197B2

Reaction notes

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