N-Methylallylamine → HCID 178457202, compound

HRID 967127Notes

Reaction equation

HRID 967127 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C@H:7]1[CH2:12][CH2:11][C@H:10]([CH2:13][N:14]([CH3:28])[S:15]([C:18]2[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][CH:19]=2)(=[O:17])=[O:16])[CH2:9][CH2:8]1.[CH2:29]([NH:32][CH3:33])[CH:30]=[CH2:31]>CO>[CH2:29]([N:32]([CH3:33])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C@H:7]1[CH2:12][CH2:11][C@H:10]([CH2:13][N:14]([CH3:28])[S:15]([C:18]2[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][CH:19]=2)(=[O:17])=[O:16])[CH2:9][CH2:8]1)[CH:30]=[CH2:31]

Participants

4

Reactant 2

HCID 69391N-MethylallylamineHCID 178484011HCID 178484011, compound

Product 1

HCID 178457202HCID 178457202, compoundYield 73.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

153 mg (0.315 mmol) trans-N-[4-(5-bromo-pentyl)-cyclohexylmethyl]-N-methyl-4-trifluoromethyl-benzenesulfonamide (example 1.6) dissolved in 2.0 ml of methanol were treated with 0.5 ml of N-allyl-methyl-amine and the reaction mixture stirred for 6 h at 50° C. It was then evaporated, poured into 50 ml of an ice/water mixture and extracted 3 times with 50 ml of dichloromethane. The combined dichloromethane phases were washed with sodium carbonate solution, dried over magnesium sulfate and evaporated under reduced pressure. The residue formed was chromatographed on silica gel with a 9:1:0.1 v/v/v mixture of dichloromethane, methanol and saturated ammonia solution as the eluent giving 0.110 g (73.3%) trans-N-{4-[5-(allyl-methyl-amino)-pentyl]-cyclohexylmethyl}-N-methyl-4-trifluoromethyl-benzenesulfonamide as colorless solid, MS: 475 (MH+).

Workup

  1. customIt was then evaporated
  2. additionpoured into 50 ml of an ice/water mixture
  3. extractionextracted 3 times with 50 ml of dichloromethane
  4. washThe combined dichloromethane phases were washed with sodium carbonate solution
  5. dry with materialdried over magnesium sulfate
  6. customevaporated under reduced pressure
  7. customThe residue formed
  8. customwas chromatographed on silica gel with a 9:1:0.1 v/v/v mixture of dichloromethane, methanol and saturated ammonia solution as the eluent

Sources & evidence

ORD record
ord-13fd538fac364b7e867c9e613fbc2f95
Source dataset
uspto-grants-2005_10
Patent number
US06953806B2

Reaction notes

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