1,2-Dichloroethane → Benzyl 4-[(4-chloro-3-methyl-phenyl)carbamoyl]piperidine-1-carboxylate

HRID 1045803

Reaction equation

HRID 1045803 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([C:17]([OH:19])=O)[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:20][C:21]1[CH:27]=[CH:26][C:24]([NH2:25])=[CH:23][C:22]=1[CH3:28].C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl>C(Cl)Cl>[Cl:20][C:21]1[CH:27]=[CH:26][C:24]([NH:25][C:17]([CH:14]2[CH2:13][CH2:12][N:11]([C:9]([O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[O:10])[CH2:16][CH2:15]2)=[O:19])=[CH:23][C:22]=1[CH3:28]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 235364-Chloro-3-methylanilineHCID 757711-HydroxybenzotriazoleHCID 7364891-Carbobenzoxy-4-piperidinecarboxylic Acid

Product 1

HCID 86685835Benzyl 4-[(4-chloro-3-methyl-phenyl)carbamoyl]piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-Benzyloxycarbonylpiperidine-4-carboxylic acid (1.00 g, 3.80 mmol) and 4-chloro-3-methyl-aniline (0.592 g, 4.18 mmol) in CH2Cl2 (5 mL) were treated with HOBT (0.582, 3.80 mmol) and EDC (1.46 g, 7.60 mmol), and stirred at rt for 16 h. The mixture was directly purified on SiO2 (50 to 100% EtOAc, hexanes) to afford the title compound. HPLC/MS: 387.2/389.1 (M+1); Rt=1.22 min (LC2).

Workup

  1. customThe mixture was directly purified on SiO2 (50 to 100% EtOAc, hexanes)

Sources & evidence

ORD record
ord-7b429f0b596b4ec1a27a93606eb29940
Source dataset
uspto-grants-2013_10
Patent number
US08569299B2

Linked notes

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