N-Methylallylamine → HCID 178457227, compound

HRID 967159Notes

Reaction equation

HRID 967159 reaction equation
[CH3:1][N:2]([C:19]([O:21][C:22]1[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][CH:23]=1)=[O:20])[CH2:3][CH2:4][C@H:5]1[CH2:10][CH2:9][C@H:8]([CH2:11][CH2:12][CH2:13]OS(C)(=O)=O)[CH2:7][CH2:6]1.[CH2:32]([NH:35][CH3:36])[CH:33]=[CH2:34]>CN(C)C(=O)C.CCOCC>[F:29][C:28]([F:31])([F:30])[C:25]1[CH:26]=[CH:27][C:22]([O:21][C:19](=[O:20])[N:2]([CH2:3][CH2:4][C@H:5]2[CH2:10][CH2:9][C@H:8]([CH2:11][CH2:12][CH2:13][N:35]([CH2:32][CH:33]=[CH2:34])[CH3:36])[CH2:7][CH2:6]2)[CH3:1])=[CH:23][CH:24]=1

Participants

5

Reactant 2

HCID 69391N-MethylallylamineHCID 178483634HCID 178483634, compound

Product 1

HCID 178457227HCID 178457227, compoundYield 65.5%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 31374DimethylacetamideSolvent

Procedure

A solution of 200 mg (0.43 mmol) trans-methanesulfonic acid 3-(4-{2-[methyl-(4-trifluoromethyl-phenoxycarbonyl)-amino]-ethyl}-cyclohexyl)-propyl ester and 0.204 ml (2.15 mmol) of allyl methyl amine in 2 ml of N,N-dimethylacetamide was stirred over night at 60° C. The reaction mixture was then taken up in ether and the ether phases were washed with water. The organic layer was dried over magnesium sulfate, concentrated under reduced pressure and the residue then chromatographed on silica gel with a 9:1 v/v mixture of dichloromethane and 1N ammonia in methanol as the eluent giving 124 mg (65.5%) trans-(2-{4-[3-(allyl-methyl-amino)-propyl]-cyclohexyl}-ethyl)-methyl-carbamic acid 4-trifluoromethyl-phenyl ester as colorless viscous oil, MS: 441 (MH+).

Workup

  1. washthe ether phases were washed with water
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customthe residue then chromatographed on silica gel with a 9:1 v/v mixture of dichloromethane and 1N ammonia in methanol as the eluent

Sources & evidence

ORD record
ord-9bcf3c439ff24ac49f13e0f0edc5910e
Source dataset
uspto-grants-2005_10
Patent number
US06953806B2

Reaction notes

Loading…