1,2-Dichloroethane → 4-(4-Chlorophenyl)-cyclohexanecarboxylic acid, methoxy-methyl amide

HRID 579596

Reaction equation

HRID 579596 reaction equation
C(Cl)CCl.[Cl:5][C:6]1[CH:11]=[CH:10][C:9]([CH:12]2[CH2:17][CH2:16][CH:15]([C:18]([OH:20])=O)[CH2:14][CH2:13]2)=[CH:8][CH:7]=1.C1C=CC2N(O)N=NC=2C=1.Cl.[CH3:32][NH:33][O:34][CH3:35].C(N(CC)CC)C>CN(C1C=CN=CC=1)C.ClCCl.O>[CH3:35][O:34][N:33]([CH3:32])[C:18]([CH:15]1[CH2:16][CH2:17][CH:12]([C:9]2[CH:10]=[CH:11][C:6]([Cl:5])=[CH:7][CH:8]=2)[CH2:13][CH2:14]1)=[O:20]

Participants

9

Reactant 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 27357924-(4-Chlorophenyl)cyclohexane-1-carboxylic acid

Product 1

HCID 885771284-(4-Chlorophenyl)-cyclohexanecarboxylic acid, methoxy-methyl amide

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

EDC (3.21 g, 16.8 mmol) was added portionwise to a stirred solution of 4-(4-chlorophenyl)-cyclohexanecarboxylic acid (2.0 g, 8.4 mmol), DMAP (5 mg), HOBt (5 mg) and N,O-dimethylhydroxylamine hydrochloride (1.63 g, 16.8 mmol) in dichloromethane (40 mL). Triethylamine (3.4 g, 4.7 mL, 33.5 mmol) was added dropwise, and the reaction mixture was stirred at room temperature. After stirring overnight the reaction mixture was poured into water and extracted with ethyl acetate (3×). The combined organic phase was washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to give 4-(4-chlorophenyl)-cyclohexanecarboxylic acid, methoxy-methyl amide as a colorless oil (1.85 g. 78%); MS (+CI): m/z for C15H20ClNO2: expected 281.1. found 282.2 (M+H)+.

Workup

  1. stirringAfter stirring overnight the reaction mixture
  2. extractionextracted with ethyl acetate (3×)
  3. washThe combined organic phase was washed with saturated aqueous sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b3567bb806dc48f794504e860688111f
Source dataset
uspto-grants-2015_05
Patent number
US09040703B2

Linked notes

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