Water → (R)-N-(2-Diethylaminoethyl)-N-[1-(4-nitrophenyl)pyrrolidin-3-yl]acetamide

HRID 1354768Notes

Reaction equation

HRID 1354768 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].C(N(CC)CC)C.[CH2:12]([N:14]([CH2:32][CH3:33])[CH2:15][CH2:16][NH:17][C@@H:18]1[CH2:22][CH2:21][N:20]([C:23]2[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[CH:25][CH:24]=2)[CH2:19]1)[CH3:13].O>ClCCl>[CH2:32]([N:14]([CH2:12][CH3:13])[CH2:15][CH2:16][N:17]([C@@H:18]1[CH2:22][CH2:21][N:20]([C:23]2[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[CH:25][CH:24]=2)[CH2:19]1)[C:1](=[O:3])[CH3:2])[CH3:33]

Participants

6

Reactant 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 67147890N,N-Diethyl-N'-[(R)-1-(4-nitrophenyl)pyrrolidin-3-yl]ethane-1,2-diamine

Product 1

HCID 67147763(R)-N-(2-Diethylaminoethyl)-N-[1-(4-nitrophenyl)pyrrolidin-3-yl]acetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Acetyl chloride (2.9 g) was dissolved in 50 ml of dry dichloromethane, mixed with 5.3 ml of triethylamine, and after addition of N,N-diethyl-N′-[(R)-1-(4-nitrophenyl)pyrrolidin-3-yl]-ethane-1,2-diamine (5.8 g), stirred at room temperature for 30 minutes. Subsequently, (LCMS check), water (10 ml) was added to the reaction, and the mixture was extracted with dichloromethane (2×10 ml). The combined organic phases were dried over magnesium sulfate, the solvent was removed, and the crude product was separated by chromatography on silica gel (dichloromethane/methanol 10:1). This resulted in the product with the molecular weight of 348.45 (C18H28N4O3); MS (ESI): 349 (M+H+).

Workup

  1. extractionthe mixture was extracted with dichloromethane (2×10 ml)
  2. dry with materialThe combined organic phases were dried over magnesium sulfate
  3. customthe solvent was removed
  4. customthe crude product was separated by chromatography on silica gel (dichloromethane/methanol 10:1)
  5. customThis resulted in the product with the molecular weight of 348.45 (C18H28N4O3)

Sources & evidence

ORD record
ord-40c1190a98a848e5ba78eb65d57f946d
Source dataset
uspto-grants-2007_05
Patent number
US07223788B2

Reaction notes

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