1,2-Dichloroethane → N-(4-aminobenzyl)pivalamide

HRID 2185957Notes

Reaction equation

HRID 2185957 reaction equation
[CH3:1][C:2]([CH3:7])([CH3:6])[C:3](O)=[O:4].[NH2:8][C:9]1[CH:16]=[CH:15][C:12]([CH2:13][NH2:14])=[CH:11][CH:10]=1.C(N(CC)CC)C.C1C=NC2N(O)N=NC=2C=1.C(Cl)CCl>C(Cl)Cl.O>[NH2:8][C:9]1[CH:16]=[CH:15][C:12]([CH2:13][NH:14][C:3](=[O:4])[C:2]([CH3:7])([CH3:6])[CH3:1])=[CH:11][CH:10]=1

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 6417Pivalic acidHCID 8471TriethylamineHCID 181649HOAtHCID 4278144-Aminobenzylamine

Product 1

HCID 18672514N-(4-aminobenzyl)pivalamideYield 83.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of trimethyl acetic acid (9.98 g, 97.7 mmol) in methylene chloride (200 ml) cooled to 0° C. is added 4-aminobenzyl amine (11.1 ml, 97.7 mmol), triethyl amine (34.1 ml, 244 mmol), HOAt (13.3 g, 97.7 mmol), and EDC (18.73 g, 97.7 mmol). The reaction mixture is allowed to slowly warm to 25° C. and stirred at this temperature for 18 hrs. The reaction mixture is diluted with water and the organic layer is extracted, washed with aqueous sodium bicarbonate and brine, dried over magnesium sulfate and concentrated in vacuo. The crude product is purified by flash chromatography (silica gel, 40% to 65% ethyl acetate in hexane) to give N-(4-amino-benzyl)-2,2-dimethyl-propionamide (16.8 g), as a pale yellow solid.

Workup

  1. extractionthe organic layer is extracted
  2. washwashed with aqueous sodium bicarbonate and brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe crude product is purified by flash chromatography (silica gel, 40% to 65% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-d6837e735f1543fab1c0e1eb248b5700
Source dataset
uspto-grants-2002_06
Patent number
US06403612B2

Reaction notes

Loading…