Benzocaine → HCID 67128324, compound

HRID 1971765Notes

Reaction equation

HRID 1971765 reaction equation
[N:1]1([CH:6]([CH3:10])[C:7]([OH:9])=O)[CH2:5][CH2:4][CH2:3][CH2:2]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH2:35]([O:37][C:38](=[O:46])[C:39]1[CH:44]=[CH:43][C:42]([NH2:45])=[CH:41][CH:40]=1)[CH3:36].CN1CCOCC1>CN(C=O)C.C(OCC)(=O)C>[N:1]1([CH:6]([CH3:10])[C:7]([NH:45][C:42]2[CH:41]=[CH:40][C:39]([C:38]([O:37][CH2:35][CH3:36])=[O:46])=[CH:44][CH:43]=2)=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

7

Reactant 4

HCID 2337BenzocaineHCID 79724-MethylmorpholineHCID 31571772-(Pyrrolidin-1-yl)propanoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 67128324HCID 67128324, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

To the 2-pyrrolidin-1-yl-propanoic acid (508 mg, 3.55 mmol) in DMF (10 mL), was added HATU (1.62 g, 4.26 mmol), 4-Amino-benzoic acid ethyl ester (645 mg, 3.90 mmol) and NMM (1.2 mL, 10.65 mmol) and stirred at 50° C. for 16 hours. The reaction mixture was diluted with ethyl acetate (50 mL) and washed with 1 N HCl, saturated NaHCO3, water, brine and dried over MgSO4. Filtration and concentration gave ethyl 4-(2-(pyrrolidin-1-yl)propanamido)benzoate.

Workup

  1. washwashed with 1 N HCl, saturated NaHCO3, water, brine
  2. dry with materialdried over MgSO4
  3. filtrationFiltration and concentration

Sources & evidence

ORD record
ord-067f79bf4ff0412fbcf33df68a88de8a
Source dataset
uspto-grants-2013_04
Patent number
US08431610B2

Reaction notes

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