Water → 4-(N-cyclohexylcarbonyl-N-(2-methyl-3-phenyl-2-(E)-propenyl)aminomethyl)-1-t-butoxycarbonylpiperidine

HRID 2110825Notes

Reaction equation

HRID 2110825 reaction equation
[CH3:1]/[C:2](=[CH:19]\[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)/[CH2:3][NH:4][CH2:5][CH:6]1[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH2:7]1.C(N(CC)CC)C.[CH:33]1([C:39](Cl)=[O:40])[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]1.O>ClCCl.CCCCCC.C(OCC)(=O)C>[CH:33]1([C:39]([N:4]([CH2:5][CH:6]2[CH2:7][CH2:8][N:9]([C:12]([O:14][C:15]([CH3:16])([CH3:17])[CH3:18])=[O:13])[CH2:10][CH2:11]2)[CH2:3]/[C:2](/[CH3:1])=[CH:19]/[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:40])[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]1

Participants

8

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 75938Cyclohexanecarbonyl chlorideHCID 63395154-(N-(2-methyl-3-phenyl-2-(E)-propenyl)aminomethyl)-1-t-butoxycarbonylpiperidine

Product 1

HCID 688638074-(N-cyclohexylcarbonyl-N-(2-methyl-3-phenyl-2-(E)-propenyl)aminomethyl)-1-t-butoxycarbonylpiperidineYield 88%

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-(N-(2-methyl-3-phenyl-2-(E)-propenyl)aminomethyl)-1-t-butoxycarbonylpiperidine (1.44 g, 4.18 mmol) and triethylamine (0.80 g, 7.9 mmol) in dichloromethane (60 mL) stirring at 0° C. under argon, was added cyclohexanecarbonyl chloride (0.75 g, 5.1 mmol) in a single portion. After 5 min the mixture was allowed to warm to room temperature. Water (0.2 mL) was added, and the mixture was evaporated under vacuum. Column chromatography (loaded as a slurry in dichloromethane, silica gel, step-wise gradient of 10% to 38% ethyl acetate in hexane) provided 4-(N-cyclohexylcarbonyl-N-(2-methyl-3-phenyl-2-(E)-propenyl)aminomethyl)-1-t-butoxycarbonylpiperidine (1.67 g, 88% yield) as a colorless gum. TLC Rf=0.19, 25% ethyl acetate in hexane.

Workup

  1. customthe mixture was evaporated under vacuum

Sources & evidence

ORD record
ord-c4634cd4fd144ea4843d99128a82b0a6
Source dataset
uspto-grants-2009_04
Patent number
US07517991B2

Reaction notes

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