1,2-Dichloroethane → HCID 59716943, compound

HRID 1992720Notes

Reaction equation

HRID 1992720 reaction equation
Cl.[CH3:2][N:3]1[CH2:8][CH2:7][C:6]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)([C:9]([OH:11])=O)[CH2:5][CH2:4]1.[CH2:18]([N:25]1[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(N(CC)CC)C.C(Cl)CCl>CN(C1C=CN=CC=1)C.ClCCl>[CH2:18]([N:25]1[CH2:30][CH2:29][N:28]([C:9]([C:6]2([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH2:5][CH2:4][N:3]([CH3:2])[CH2:8][CH2:7]2)=[O:11])[CH2:27][CH2:26]1)[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 759941-BenzylpiperazineHCID 68626903HCID 68626903, compound

Product 1

HCID 59716943HCID 59716943, compoundYield 79.5%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 1-methyl-4-phenylpiperidine-4-carboxylic acid hydrochloride (1.35 g, 5 mmol), benzyl piperazine 0.88 g (5 mmol), triethylamine 1 ml and EDC 1.91 g (10 mmol) and DMAP (catalytic) in 40 ml dichloromethane was stirred at room temperature overnight, concentrated, added water and extracted with ethyl acetate 2'50 ml. The combined organic solution was dried over sodium sulfate and concentrated. The residue was applied to flash column chromatography using methylene chloride and methanol (100:10) as eluents to give 1.5 g of desired product.

Workup

  1. concentrationconcentrated
  2. additionadded water
  3. extractionextracted with ethyl acetate 2'50 ml
  4. dry with materialThe combined organic solution was dried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-055e81a30d9240388036bd4eae983f62
Source dataset
uspto-grants-2010_01
Patent number
US07649092B2

Reaction notes

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