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Acetyl chloride → N-{2-chloro-4-[3-(3,5-dichlorophenyl)-3-(trifluoromethyl)pyrrolidin-1-yl]benzyl}acetamide

HRID 1930520
Notes
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Reaction equation

HRID 1930520 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([N:8]2[CH2:12][CH2:11][C:10]([C:17]3[CH:22]=[C:21]([Cl:23])[CH:20]=[C:19]([Cl:24])[CH:18]=3)([C:13]([F:16])([F:15])[F:14])[CH2:9]2)[CH:5]=[CH:4][C:3]=1[CH2:25][NH2:26].C(N(CC)CC)C.[C:34](Cl)(=[O:36])[CH3:35]>O1CCCC1.C(OC)(C)(C)C>[Cl:1][C:2]1[CH:7]=[C:6]([N:8]2[CH2:12][CH2:11][C:10]([C:17]3[CH:18]=[C:19]([Cl:24])[CH:20]=[C:21]([Cl:23])[CH:22]=3)([C:13]([F:15])([F:14])[F:16])[CH2:9]2)[CH:5]=[CH:4][C:3]=1[CH2:25][NH:26][C:34](=[O:36])[CH3:35]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 453777791-(2-Chloro-4-[3-(3,5-dichlorophenyl)-3-(trifluoromethyl)pyrrolidin-1-yl]phenyl}methanamine

Product 1

HCID 86652388N-{2-chloro-4-[3-(3,5-dichlorophenyl)-3-(trifluoromethyl)pyrrolidin-1-yl]benzyl}acetamideYield 84.3%

Reagents, catalysts & solvents 2

HCID 8028
Tetrahydrofuran
Solvent
HCID 15413tert-Butyl methyl etherSolvent

Procedure

To the solution of 1-{2-chloro-4-[3-(3,5-dichlorophenyl)-3-(trifluoromethyl)pyrrolidin-1-yl]phenyl}methanamine (0.12 g) and triethylamine (0.04 g) in tetrahydrofuran was added dropwise acetyl chloride (0.02 g), and the mixture was stirred for one hour at room temperature. The reaction solution was diluted with t-butylmethylether and then washed with water and brine. The organic layer was dried over anhydrous magnesium sulfate. The solvent was distilled away under the reduced pressure, and the residue was then purified by silica gel chromatography to yield N-{2-chloro-4-[3-(3,5-dichlorophenyl)-3-(trifluoromethyl)pyrrolidin-1-yl]benzyl}acetamide (0.1 g). 1H-NMR (CDCl3) δ: 1.98-2.01 (3H, m), 2.50-2.58 (1H, m), 2.82-2.87 (1H, m), 3.45-3.51 (2H, m), 3.74 (1H, d), 4.02 (1H, d), 4.41 (2H), 6.43-6.46 (1H, m), 6.58-6.59 (1H, m), 7.26-7.38 (4H, m)

Workup

  1. washwashed with water and brine
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. distillationThe solvent was distilled away under the reduced pressure
  4. customthe residue was then purified by silica gel chromatography

Sources & evidence

ORD record
ord-36f939e72e074d1d9e46e86853d48390
Source dataset
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08188122B2

Reaction notes

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