Dimethylamine → HCID 178447108, compound

HRID 2057347Notes

Reaction equation

HRID 2057347 reaction equation
[CH3:1][N:2]([C@H:16]1[CH2:21][CH2:20][C@H:19]([O:22][CH2:23][CH2:24][CH2:25][C:26](=O)[CH3:27])[CH2:18][CH2:17]1)[S:3]([C:6]1[CH:11]=[CH:10][C:9]([C:12]([F:15])([F:14])[F:13])=[CH:8][CH:7]=1)(=[O:5])=[O:4].[CH3:29][NH:30][CH3:31].[BH3-]C#N.[Na+].O>C(O)C.CC([O-])C.CC([O-])C.CC([O-])C.CC([O-])C.[Ti+4]>[CH3:29][N:30]([CH3:31])[CH:26]([CH3:27])[CH2:25][CH2:24][CH2:23][O:22][C@H:19]1[CH2:20][CH2:21][C@H:16]([N:2]([CH3:1])[S:3]([C:6]2[CH:11]=[CH:10][C:9]([C:12]([F:15])([F:14])[F:13])=[CH:8][CH:7]=2)(=[O:5])=[O:4])[CH2:17][CH2:18]1

Participants

7

Reactant 4

HCID 674Dimethylamine2×HCID 962WaterHCID 5003444Sodium cyanoborohydrideHCID 178467851HCID 178467851, compound

Product 1

HCID 178447108HCID 178447108, compoundYield 18%

Reagents, catalysts & solvents 2

HCID 11026Titanium isopropoxideCatalyst2×HCID 702EthanolSolvent

Procedure

70 mg (0.17 mmol) trans-N-Methyl-N-[4-(4-oxo-pentyloxy)-cyclohexyl]-4-trifluoromethyl-benzenesulfonamide were treated with 31 μM (30% in ethanol, 0.17 mmol) dimethylamine and 61 μM (0.17 mmol) tetraisopropyl orthotitanate. The solution was stirred at RT for 18 h, additional 31 μM (30% in ethanol, 0.17 mmol) dimethylamine and 61 μM (0.17 mmol) tetraisopropyl orthotitanate were added and stirring was continued for 2 h. The mixture was diluted with 1.7 ml ethanol and 7 mg (0.1 mmol) NaCNBH3 were added, and stirring was continued over night. 0.35 ml water was added and the suspension filtered and evaporated. The residue was purified by column chromatography with CH2Cl2/MeOH 9:1 to give 13.2 mg (18%) trans-N-[4-(4-Dimethylamino-pentyloxy)-cyclohexyl]-N-methyl-4-trifluoromethyl-benzenesulfonamide as colorless oil, MS: 451 (MH+).

Workup

  1. stirringstirring
  2. waitwas continued for 2 h
  3. additionwere added
  4. stirringstirring
  5. waitwas continued over night
  6. filtrationthe suspension filtered
  7. customevaporated
  8. customThe residue was purified by column chromatography with CH2Cl2/MeOH 9:1

Sources & evidence

ORD record
ord-0fbfba0047a9409f877496ace3a3ebda
Source dataset
uspto-grants-2008_02
Patent number
US07335687B2

Reaction notes

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