1,2-Dichloroethane → N-(1-Benzhydryl-pyrrolidin-3-ylmethyl)-3,3-diphenyl-propionamide

HRID 1295866Notes

Reaction equation

HRID 1295866 reaction equation
[CH:1]([N:14]1[CH2:18][CH2:17][CH:16]([CH2:19][NH2:20])[CH2:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:21]1([CH:27]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH2:28][C:29](O)=[O:30])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(Cl)CCl>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH:1]([N:14]1[CH2:18][CH2:17][CH:16]([CH2:19][NH:20][C:29](=[O:30])[CH2:28][CH:27]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH2:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 111,2-DichloroethaneHCID 64798Diphenylpropionic acidHCID 43344287C-(1-Benzhydryl-pyrrolidin-3-yl)-methylamine

Product 1

HCID 11751858N-(1-Benzhydryl-pyrrolidin-3-ylmethyl)-3,3-diphenyl-propionamide

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of C-(1-Benzhydryl-pyrrolidin-3-yl)-methylamine (0.26 g, 0.98 mmol) in dry CH2Cl2 (25 ml) was added 3,3-diphenylpropionic acid (0.22 g, 0.98 mmol) under nitrogen. To the reaction was added EDC (0.37 g, 1.95 mmol) and DMAP (cat) and the reaction mixture stirred under nitrogen at room temperature overnight. The reaction was then concentrated under reduced pressure. The residue dissolved in ethyl acetate: water (10:1) (100 ml). The organic was washed with water (20 ml, 2×) and 10% NaOH (20 ml) and dried over MgSO4 and evaporated to dryness. The resulting residue was purified by column chromatography using CH2Cl2:CH3OH (15:1) to give a desired product in good yield

Workup

  1. concentrationThe reaction was then concentrated under reduced pressure
  2. dissolutionThe residue dissolved in ethyl acetate: water (10:1) (100 ml)
  3. washThe organic was washed with water (20 ml, 2×) and 10% NaOH (20 ml)
  4. dry with materialdried over MgSO4
  5. customevaporated to dryness
  6. customThe resulting residue was purified by column chromatography

Sources & evidence

ORD record
ord-3813c9590fda4cc286aa649696aa6c27
Source dataset
uspto-grants-2007_07
Patent number
US07244758B2

Reaction notes

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