1,2-Dichloroethane → HCID 178502722, compound

HRID 579587Notes

Reaction equation

HRID 579587 reaction equation
C(Cl)CCl.[Cl:5][C:6]1[CH:22]=[CH:21][C:9]([C:10]([C@@H:12]2[CH2:17][CH2:16][C@H:15]([C:18]([OH:20])=O)[CH2:14][CH2:13]2)=[O:11])=[CH:8][CH:7]=1.C1C=CC2N(O)N=NC=2C=1.Cl.[CH3:34][NH:35][O:36][CH3:37].C(N(CC)CC)C>CN(C1C=CN=CC=1)C.ClCCl.O>[CH3:37][O:36][N:35]([CH3:34])[C:18]([C@H:15]1[CH2:14][CH2:13][C@@H:12]([C:10](=[O:11])[C:9]2[CH:8]=[CH:7][C:6]([Cl:5])=[CH:22][CH:21]=2)[CH2:17][CH2:16]1)=[O:20]

Participants

9

Reactant 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 178525727HCID 178525727, compound

Product 1

HCID 178502722HCID 178502722, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

EDC (2.87 g, 15.0 mmol) was added portionwise to a stirred solution of cis-4-(4-chlorobenzoyl)-cyclohexanecarboxylic acid (2.0 g, 7.5 mmol), DMAP (5 mg), HOBt (5 mg) and N,O-dimethylhydroxylamine hydrochloride (1.46 g, 15 mmol) in dichloromethane (40 mL). Triethylamine (2.28 g, 3.14 mL, 22.5 mmol) was added dropwise, and the reaction mixture was stirred at room temperature overnight. The resulting solution 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 cis-4-(4-chlorobenzoyl)-cyclohexanecarboxylic acid, methoxy-methyl amide as a colorless oil (1.6 g. 69%); 1H NMR (CDCl3, 300 MHz) δ 7.82 (d, J=8.5 Hz, 2H,), 7.41 (d, J=8.5 Hz, 2H), 3.69 (s, 3H), 3.35 (quin, J=5 Hz, 1H), 3.16 (s, 3H), 2.80 (sept, J=4 Hz, 1H), 2.15 (m, 2H), 1.89 (m, 2H), 1.72 (m, 4H).

Workup

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

Sources & evidence

ORD record
ord-14a48c929f1a49d9bb3956ac1bf16a1c
Source dataset
uspto-grants-2015_05
Patent number
US09040703B2

Reaction notes

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