1,2-Dichloroethane → (R)-N-(1-Benzyl-pyrrolidin-3-yl)-2-diphenylamino-N-methyl-acetamide

HRID 1786543

Reaction equation

HRID 1786543 reaction equation
[C:1]([N:9]1[CH2:13][CH2:12][C@@H:11]([NH:14][CH3:15])[CH2:10]1)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:16]1([N:22]([CH2:29][C:30](O)=[O:31])[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(Cl)CCl>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH2:1]([N:9]1[CH2:13][CH2:12][C@@H:11]([N:14]([CH3:15])[C:30](=[O:31])[CH2:29][N:22]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 111,2-DichloroethaneHCID 735138(Diphenylamino)acetic acidHCID 70216545HCID 70216545, compound

Product 1

HCID 57597569(R)-N-(1-Benzyl-pyrrolidin-3-yl)-2-diphenylamino-N-methyl-acetamideYield 101.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of (R)-(1-benzoyl-pyrrolidin-3-yl)-methyl-amine(0.32 g, 1.68 mmol) in dry CH2Cl2 (20 ml) was added diphenylaminoacetic acid (0.38 g, 1.68 mmol) under nitrogen. To the reaction was added EDC (0.65 g, 3.36 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 was dissolved in ethyl acetate: water (10:1) (100 ml). The organic was washed with water (25 ml, 2×) and 10% NaOH (25 ml), dried over MgSO4 and evaporated to dryness. The resulting residue was purified by column chromatography using CH2Cl2:CH3OH (15:1) to give 0.68 g of desired product.

Workup

  1. concentrationThe reaction was then concentrated under reduced pressure
  2. dissolutionThe residue was dissolved in ethyl acetate: water (10:1) (100 ml)
  3. washThe organic was washed with water (25 ml, 2×) and 10% NaOH (25 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-fa9c619af59e4c759fc0932583cffe39
Source dataset
uspto-grants-2009_03
Patent number
US07507760B2

Linked notes

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