N-Methylpropylamine → HCID 178457234, compound

HRID 25635Notes

Reaction equation

HRID 25635 reaction equation
[Cl:1][C:2]1[CH:26]=[CH:25][C:5]([O:6][C:7]([N:9]([CH3:24])[C@H:10]2[CH2:15][CH2:14][C@H:13]([C:16]#[C:17][CH2:18]OS(C)(=O)=O)[CH2:12][CH2:11]2)=[O:8])=[CH:4][CH:3]=1.[CH3:27][NH:28][CH2:29][CH2:30][CH3:31]>CC(N(C)C)=O>[Cl:1][C:2]1[CH:26]=[CH:25][C:5]([O:6][C:7](=[O:8])[N:9]([CH3:24])[C@H:10]2[CH2:15][CH2:14][C@H:13]([C:16]#[C:17][CH2:18][N:28]([CH3:27])[CH2:29][CH2:30][CH3:31])[CH2:12][CH2:11]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 12315N-MethylpropylamineHCID 178485964HCID 178485964, compound

Product 1

HCID 178457234HCID 178457234, compoundYield 81.2%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

A solution of 235 mg (corresponds to 0.5 mmol) of trans-Methanesulfonic acid 3-{4-[(4-chloro-phenoxycarbonyl)-methyl-amino]-cyclohexyl}-prop-2-ynyl ester in 2.5 ml of DMA was cooled at 0° C., treated with 0.76 ml (1 mmol) of N-methylpropylamine and stirred over night at RT. The solvent was evaporated and the residue extracted with aqueous saturated NaHCO3/Et2O (3×). The organic phase was dried with Na2SO4, filtered and evaporated. Purification by flash column chromatography on silica gel (CH2Cl2/MeOH 98:2) gave 153 mg (81%) of pure trans-Methyl-{4-[3-(methyl-propyl-amino)-prop-1-ynyl]-cyclohexyl}-carbamic acid 4-chloro-phenyl ester, MS: 377 (MH+, 1Cl).

Workup

  1. customThe solvent was evaporated
  2. extractionthe residue extracted with aqueous saturated NaHCO3/Et2O (3×)
  3. dry with materialThe organic phase was dried with Na2SO4
  4. filtrationfiltered
  5. customevaporated
  6. customPurification by flash column chromatography on silica gel (CH2Cl2/MeOH 98:2)

Sources & evidence

ORD record
ord-04f860aa141d48b8a3ce72a94de26847
Source dataset
uspto-grants-2005_02
Patent number
US06858651B2

Reaction notes

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