N-Methylallylamine → HCID 178457216, compound

HRID 25624

Reaction equation

HRID 25624 reaction equation
[Cl:1][C:2]1[CH:27]=[CH:26][C:5]([O:6][C:7]([N:9]([CH3:25])[C@H:10]2[CH2:15][CH2:14][C@H:13]([CH2:16][CH2:17][CH2:18][CH2:19]OS(C)(=O)=O)[CH2:12][CH2:11]2)=[O:8])=[CH:4][CH:3]=1.[CH2:28]([NH:31][CH3:32])[CH:29]=[CH2:30]>CO>[Cl:1][C:2]1[CH:27]=[CH:26][C:5]([O:6][C:7](=[O:8])[N:9]([C@H:10]2[CH2:15][CH2:14][C@H:13]([CH2:16][CH2:17][CH2:18][CH2:19][N:31]([CH2:28][CH:29]=[CH2:30])[CH3:32])[CH2:12][CH2:11]2)[CH3:25])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 69391N-MethylallylamineHCID 178485963HCID 178485963, compound

Product 1

HCID 178457216HCID 178457216, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 219 mg (0.524 mmol) of trans-Methanesulfonic acid 4-{4-[(4-chloro-phenoxycarbonyl)-methyl-amino]-cyclohexyl}-butyl ester and 0.48 ml of N-allyl methyl-amine in 1 ml of MeOH was stirred over night at RT, and for 2 h under reflux. After concentration of the reaction-mixture in vacuo, the crude product was purified by chromatography over silica gel with EtOAc/H2O/AcOH/Aceton (6:2:1:1) to give 165 mg (80%) of clean trans-{4-[4-(Allyl-methyl-amino)-butyl]-cyclohexyl}-methyl-carbamic acid 4-chloro-phenyl ester, MS: 393 (MH+, 1Cl).

Workup

  1. temperaturefor 2 h under reflux
  2. customAfter concentration of the reaction-mixture in vacuo, the crude product was purified by chromatography over silica gel with EtOAc/H2O/AcOH/Aceton (6:2:1:1)

Sources & evidence

ORD record
ord-c17a192ecdfe4fe2ac680189f44108ad
Source dataset
uspto-grants-2005_02
Patent number
US06858651B2

Linked notes

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