1-Methylpyrrolidine → HCID 86662339, compound

HRID 921997

Reaction equation

HRID 921997 reaction equation
[Cl:1][CH2:2][C:3]([O:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13](=[O:15])[CH3:14])=[CH:8][CH:7]=1)=[O:4].[CH3:16][N:17]1[CH2:21][CH2:20][CH2:19][CH2:18]1>C(OCC)(=O)C>[Cl-:1].[C:13]([NH:12][C:9]1[CH:10]=[CH:11][C:6]([O:5][C:3](=[O:4])[CH2:2][N+:17]2([CH3:16])[CH2:21][CH2:20][CH2:19][CH2:18]2)=[CH:7][CH:8]=1)(=[O:15])[CH3:14]

Participants

4

Reactant 2

HCID 84541-MethylpyrrolidineHCID 132776644-Acetamidophenyl chloroacetate

Product 1

HCID 86662339HCID 86662339, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

4-Acetamidophenyl 2-chloroacetate [2] (1.138 g, 5 mmol) and N-methylpyrrolidine (0.511 g, 6 mmol) were suspended in 50 ml of anhydrous ethyl acetate and refluxed for 48 hrs. After cooling to room temperature the white precipitate was filtered, washed with ethylacetate and diethylether and dried under reduced pressure to give [4] in 97% yield. The product was pure according to 1H NMR and was directly subjected to the next step without further purification. The desired compound is isolated as a colourless powder. 1H-NMR (300 MHz, d6-DMSO) δ(ppm)=10.48 (s, 1H), 7.72 (d, J=8.90 Hz, 2H), 7.17 (d, J=8.90 Hz, 2H), 4.91 (s, 2H), 3.75 (m, 4H), 3.26 (s, 3H), 2.13 (m, 4H), 2.06 (s, 3H). 13C-NMR (75 MHz, d6-DMSO) δ(ppm)=168.8, 164.8, 144.4, 138.2, 121.9, 120.2, 65.5, 62.0, 49.7, 24.3, 21.7. mp 186° C. (dec), T5%onset 197° C.

Workup

  1. temperaturerefluxed for 48 hrs
  2. filtrationwas filtered
  3. washwashed with ethylacetate and diethylether
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-d2b8043ec5c04a5d8306d09fefe175c4
Source dataset
uspto-grants-2016_03
Patent number
US09278134B2

Linked notes

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