Triethylamine → HCID 3599105, compound

HRID 2367941Notes

Reaction equation

HRID 2367941 reaction equation
Cl.Cl.C1([C@H](N[C@H]2CCNC2)C)C2C(=CC=CC=2)C=CC=1.ON1[C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=2N=N1.[CH2:31]([N:33]([CH2:36][CH3:37])[CH2:34][CH3:35])[CH3:32].C(=O)(O)[O-:39].[Na+]>CN(C=O)C.C(OCC)(=O)C>[C:25]1([CH2:32][C:31]([N:33]2[CH2:36][CH2:37][CH2:35][CH2:34]2)=[O:39])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 67408696(S)-3-[(R)-1-(naphthalen-1-yl)ethylamino]pyrrolidine dihydrochloride

Product 1

HCID 3599105HCID 3599105, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To solution of 125.3 mg of (S)-3-[(R)-1-(naphthalen-1-yl)ethylamino]pyrrolidine dihydrochloride in 5 ml of DMF were added 81.6 mg of (3-trifluoromethyl)phenylacetic acid, 84.3 mg of 1-[3-(dimethylaminopropyl)]-3-ethylcarbodiimide hydrochloride, 67.3 mg of 1-hydroxybenzotriazole, and 153 μl of triethylamine, and the reaction mixture was stirred at room temperature for 16 hours. To the reaction mixture were added a saturated aqueous sodium bicarbonate solution and ethyl acetate, the mixture was stirred and the liquids were separated. The organic layer was washed with water and then dried, the solvent was evaporated, and the residue was purified by thin layer silica gel chromatography (chloroform:methanol=19:1) to obtain 145.7 mg of (S)-3-[(R)-(naphthalen-1-yl)ethylamino]-1 -3-trifluoromethyl)phenylacetylpyrrolidine (Example 5.017 in the following Table C).

Workup

  1. stirringthe mixture was stirred
  2. customthe liquids were separated
  3. washThe organic layer was washed with water
  4. customdried
  5. customthe solvent was evaporated
  6. customthe residue was purified by thin layer silica gel chromatography (chloroform:methanol=19:1)

Sources & evidence

ORD record
ord-2168aeed7e4144dfa772320828163104
Source dataset
uspto-grants-2014_04
Patent number
US08703721B2

Reaction notes

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