1,2-Dichloroethane → 1-[4-(3-Methyl-[1,2,4]oxadiazol-5-yl)-benzoyl]-4-phenyl-piperidine-4-carboxylic acid methyl ester

HRID 2189980Notes

Reaction equation

HRID 2189980 reaction equation
[CH3:1][C:2]1[N:6]=[C:5]([C:7]2[CH:15]=[CH:14][C:10]([C:11]([OH:13])=O)=[CH:9][CH:8]=2)[O:4][N:3]=1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.C(N(CC)CC)C.[CH3:37][O:38][C:39]([C:41]1([C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)[CH2:46][CH2:45][NH:44][CH2:43][CH2:42]1)=[O:40]>C(Cl)Cl.C(OCC)(=O)C.CCCCCCC>[CH3:37][O:38][C:39]([C:41]1([C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)[CH2:42][CH2:43][N:44]([C:11](=[O:13])[C:10]2[CH:9]=[CH:8][C:7]([C:5]3[O:4][N:3]=[C:2]([CH3:1])[N:6]=3)=[CH:15][CH:14]=2)[CH2:45][CH2:46]1)=[O:40]

Participants

9

Reactant 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 545827Methyl 4-phenylpiperidine-4-carboxylateHCID 221101114-(3-Methyl-1,2,4-oxadiazol-5-yl)benzoic acid

Product 1

HCID 332468811-[4-(3-Methyl-[1,2,4]oxadiazol-5-yl)-benzoyl]-4-phenyl-piperidine-4-carboxylic acid methyl esterYield 85.1%

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolventHCID 8900HeptaneSolvent

Procedure

To a mixture of 4-(3-methyl-1,2,4-oxadiazol-5-yl)benzoic acid (408 mg, 2.0 mmol) (commercially available), EDC (614 mg, 3.2 mmol), HOBT (490 mg, 3.2 mmol) and triethylamine (1031 μL, 7.4 mmol) in DCM (6 ml) at room temperature was added slowly a solution of 4-phenyl-piperidine-4-carboxylic acid methyl ester (439 mg, 2.0 mmol) in DCM (3 mL). The reaction mixture was stirred at room temperature for 12 h. The reaction mixture was subjected to flash chromatography with n-heptane and ethyl acetate over a 70 g silica gel column to give 690 mg 1-[4-(3-methyl-[1,2,4]oxadiazol-5-yl)-benzoyl]-4-phenyl-piperidine-4-carboxylic acid methyl ester. MS ISP (m/e): 406.3 [(M+H)+].

Sources & evidence

ORD record
ord-3197b47e47494b80aae6e036f12ad8fd
Source dataset
uspto-grants-2012_12
Patent number
US08324250B2

Reaction notes

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