1,2-Dichloroethane → HCID 88577121, compound

HRID 579561Notes

Reaction equation

HRID 579561 reaction equation
C(Cl)CCl.[Cl:5][C:6]1[CH:11]=[CH:10][C:9]([N:12]2[CH2:16][CH2:15][CH:14]([C:17]([OH:19])=O)[CH2:13]2)=[CH:8][CH:7]=1.Cl.[CH3:21][NH:22][O:23][CH3:24].C(N(CC)CC)C>CN(C1C=CN=CC=1)C.ClCCl.O>[CH3:24][O:23][N:22]([CH3:21])[C:17]([CH:14]1[CH2:15][CH2:16][N:12]([C:9]2[CH:10]=[CH:11][C:6]([Cl:5])=[CH:7][CH:8]=2)[CH2:13]1)=[O:19]

Participants

8

Reactant 4

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 510638331-(4-Chlorophenyl)pyrrolidine-3-carboxylic acid

Product 1

HCID 88577121HCID 88577121, compoundYield 98%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

EDC (1.70 g, 8.86 mmol) was added portionwise to a stirred solution of 1-(4-chloro-phenyl)-pyrrolidine-3-carboxylic acid (1.0 g, 4.43 mmol), DMAP (5 mg) and N,O-dimethylhydroxylamine hydrochloride (865 mg, 8.86 mmol) in dichloromethane (20 mL). To this solution was added dropwise triethylamine (1.79 g, 2.47 mL, 17.7 mmol) and the reaction mixture was stirred at room temperature overnight. At the end of stirring, 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 the title compound as a white solid (1.10 g. 98%); 1H NMR (CDCl3, 300 MHz) δ 7.14 (d, J=8 Hz, 2H), 6.46 (d, J=8 Hz, 2H), 3.74 (s, 3H), 3.50-3.56 (m, 2H), 3.40-3.47 (m, 2H), 3.33 (m, 1H), 3.23 (s, 3H), 2.20-2.36 (m, 2H).

Workup

  1. stirringAt the end of stirring
  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-fc294f25cf3e477d95d194b2ffb0c70c
Source dataset
uspto-grants-2015_05
Patent number
US09040703B2

Reaction notes

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