1,2-Dichloroethane → N-(3-(azepan-1-yl)propyl)-1-((2-(4-chlorophenyl)-5-methyloxazol-4-yl)methyl)piperidine-4-carboxamide

HRID 1025405Notes

Reaction equation

HRID 1025405 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]([CH3:23])=[C:11]([CH2:13][N:14]3[CH2:19][CH2:18][CH:17]([C:20](O)=[O:21])[CH2:16][CH2:15]3)[N:12]=2)=[CH:4][CH:3]=1.[N:24]1([CH2:31][CH2:32][CH2:33][NH2:34])[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1.CCN(C(C)C)C(C)C.C(Cl)CCl>CN(C=O)C>[N:24]1([CH2:31][CH2:32][CH2:33][NH:34][C:20]([CH:17]2[CH2:16][CH2:15][N:14]([CH2:13][C:11]3[N:12]=[C:8]([C:5]4[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=4)[O:9][C:10]=3[CH3:23])[CH2:19][CH2:18]2)=[O:21])[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 81531DiisopropylethylamineHCID 27643953-(Azepan-1-yl)propan-1-amineHCID 209671331-((2-(4-Chlorophenyl)-5-methyloxazol-4-yl)methyl)piperidine-4-carboxylic acid

Product 1

HCID 20859820N-(3-(azepan-1-yl)propyl)-1-((2-(4-chlorophenyl)-5-methyloxazol-4-yl)methyl)piperidine-4-carboxamideYield 85%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-((2-(4-chlorophenyl)-5-methyloxazol-4-yl)methyl)piperidine-4-carboxylic acid (0.25 g, 0.75 mmole), 3-(Azepan-1-yl)propan-1-amine (0.33 g) and DIPEA (0.32 mL) in DMF (5 mL) was added EDC (0.153 g). The reaction solution was stirred at room temperature overnight. The solvent removed and EtOAc (100 mL) was added. The organic layer was washed with saturated sodium bicarbonate (50 mL), water (50 mL) and dried over anhydrous magnesium sulfate. After filtration, the residue after concentration of the filtrate was crystallized from EtOAc/Hexane to provide the N-(3-(azepan-1-yl)propyl)-1-((2-(4-chlorophenyl)-5-methyloxazol-4-yl)methyl)piperidine-4-carboxamide as white solid (0.30 g, 85%). H1NMR (300 MHz, CDCl3), ppm: 7.94 (d, 2H), 7.49 (m, 1H), 7.39 (d, 2H), 3.44 (s, 2H), 3.36 (m, 2H), 2.99 (d, 2H), 2.67 (m, 4H), 2.60 (t, 2H), 2.39 (s, 3H), 2.07 (m, 3H), 1.83 (m, 4H), 1.65 (m, 10H). MS (ESI+) M/z: 473, 475 (M+H).

Workup

  1. customThe solvent removed
  2. additionEtOAc (100 mL) was added
  3. washThe organic layer was washed with saturated sodium bicarbonate (50 mL), water (50 mL)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationAfter filtration
  6. customthe residue after concentration of the filtrate was crystallized from EtOAc/Hexane

Sources & evidence

ORD record
ord-d2325b91b2ba4bbea4252a52d684c21e
Source dataset
uspto-grants-2014_05
Patent number
US08729081B2

Reaction notes

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